Heterocyclic dihydrazole compounds and their use for controlling fungal plant diseases

ABSTRACT

Compounds of Formula I, and their N-oxides and agriculturally suitable salts, are disclosed which are useful as fungicides ##STR1## In said formula, E is a ring system selected from certain 5- to 12-membered monocyclic and fused bicyclic aromatic heterocyclic ring systems, or an optionally substituted naphthalene ring as defined in the disclosure; 
     A is O; S; N; NR 5  ; or CR 14  ; 
     G is C or N; provided that when G is C, then A is O, S or NR 5  and the floating double bond is attached to G; and when G is N, then A is N or CR 14  and the floating double bond is attached to A; 
     W is O; S; NH; N(C 1  -C 6  alkyl); or NO(C 1  -C 6  alkyl); 
     X is OR 1  ; S(O) m  R 1  ; or halogen; 
     R 1  is C 1  -C 6  alkyl; C 1  -C 6  haloalkyl; C 2  -C 6  alkenyl; C 2  -C 6  haloalkenyl; C 2  -C 6  alkynyl; C 2  -C 6  haloalkynyl; C 3  -C 6  cycloalkyl; C 2  -C 4  alkylcarbonyl; or C 2  -C 4  alkoxycarbonyl; 
     R 2  is H; C 1  -C 6  alkyl; C 1  -C 6  haloalkyl; C 2  -C 6  alkenyl; C 2  -C 6  haloalkenyl; C 2  -C 6  alkynyl; C 2  -C 6  haloalkynyl; C 3  -C 6  cycloalkyl; C 2  -C 4  alkylcarbonyl; C 2  -C 4  alkoxycarbonyl; hydroxy; C 1  -C 2  alkoxy; or acetyloxy; 
     R 5  is H; C 1  -C 6  alkyl; C 1  -C 6  haloalkyl; C 2  -C 6  alkenyl; C 2  -C 6  haloalkenyl; C 2  -C 6  alkynyl; C 2  -C 6  haloalkynyl; C 3  -C 6  cycloalkyl; C 2  -C 4  alkylcarbonyl; or C 2  -C 4  alkoxycarbonyl; and 
     Y, Z, R 14  and m are as defined in the disclosure. 
     Also disclosed are compositions containing the compounds of Formula I and a method for controlling plant diseases caused by fungal plant pathogens which involves applying an effective amount of a compound of Formula I.

This application is a national filing under 35 USC 371 of InternationalApplication No. PCT/US96/06533 filed May 8, 1996 which is acontinuation-in-part of U.S. patent application Ser. No. 08/443,295filed May 17, 1995 (now abandoned).

BACKGROUND OF THE INVENTION

This invention relates to certain cyclic amides, their N-oxides,agriculturally suitable salts and compositions, and methods of their useas fungicides.

The control of plant diseases caused by fungal plant pathogens isextremely important in achieving high crop efficiency. Plant diseasedamage to ornamental, vegetable, field, cereal, and fruit crops cancause significant reduction in productivity and thereby result inincreased costs to the consumer. Many products are commerciallyavailable for these purposes, but the need continues for new compoundswhich are more effective, less costly, less toxic, environmentally saferor have different modes of action.

WO 95/01973 discloses certain heterocyclic amides and esters of Formulai as fungicides ##STR2## wherein Ar is substituted aryl or heteroaryl;

R¹ is alkyl or haloalkyl;

R² and R³ are independently, among others, hydrogen, halogen, cyano,nitro, alkyl, alkoxy, alkylthio, alkenyl, alkenyloxy, alkynyl,alkynyloxy, haloallyl, haloalkoxy, haloalkenyl, haloalkynyl,alkoxycarbonyl, or substituted phenyl;

A is --O--; --CH═CH--; --C.tbd.C--; --CH₂ O--; --OCH₂ --; --CH₂ S(O)_(n)--; --S(O)_(n) CH₂ --; --S(O)_(n) --; --C(R⁴)═N--O--; --C(R⁴)═N--OCH₂--; or --NR⁶ --;

Z is OR⁵ or NR⁶ R⁷ ;

R⁴ is H, alkyl, haloalkyl, cycloalkyl or cyano;

R⁵ is alkyl or haloalkyl;

R⁶ and R⁷ are independently H, alkyl, haloalkyl or alkoxy; and

n is 0, 1 or 2.

The cyclic amides of the present invention are not disclosed therein.

J. Heterocyclic Chem., (1987), 24, 465, J. Heterocyclic Chem., (1988),25, 1307, and Australian J. Chem., (1977), 30 (8), 1815 disclose4-nitrophenyl isoxazoles (ii), phenyl pyrazolones (iii), and arylisothiazolinones (iv) respectively. ##STR3##

However, no utility as fungicides is alleged and the cyclic amides ofthe present invention are not disclosed therein.

SUMMARY OF THE INVENTION

This invention is directed to compounds of Formula I including allgeometric and stereoisomers, N-oxides, and agriculturally suitable saltsthereof, agricultural compositions containing them and their use asfungicides: ##STR4## wherein E is a ring system selected from:

i) 5 to 12-membered monocyclic and fused bicyclic aromatic heterocyclicring systems, each heterocyclic ring system containing 1 to 6heteroatoms independently selected from the group nitrogen, oxygen, andsulfur, provided that each heterocyclic ring system contains no morethan 4 nitrogens, no more than 2 oxygens, and no more than 2 sulfurs,each fused bicyclic ring system optionally containing one nonaromaticring that optionally includes one or two Q as ring members andoptionally includes one or two ring members independently selected fromC(═O) and S(O)₂, provided that G is attached to an aromatic ring, andwhen G and Y are attached to the same ring, then G and Y are attached toadjacent ring members, each aromatic heterocyclic ring system optionallysubstituted with one of R³, R⁴, or both R³ and R⁴ ; and

ii) a naphthalene ring, provided that when G and Y are attached to thesame ring, then G and Y are attached to adjacent ring members, thenaphthalene ring optionally substituted with one of R³, R⁴, or both R³and R⁴, provided that when G is attached to the 1, 4, 5, or 8 positionof the naphthalene ring and Z is C₁ -C₁₀ alkyl, C₂ -C₁₀ alkenyl, C₂ -C₁₀alkynyl or phenyl each substituted with R⁹ and optionally substitutedwith one or more R¹⁰, then Y is other than --O--, --S(O)_(n) --,--C(═O)--, --CHR⁶ --, --CHR⁶ CHR⁶ --, --CR⁶ ═CR⁶ --, --C.tbd.C--,--OCHR¹⁵ --, --S(O)_(n) CHR¹⁵ -- or a direct bond;

A is O; S; N; NR⁵ ; or CR¹⁴ ;

G is C or N; provided that when G is C, then A is O, S or NR⁵ and thefloating double bond is attached to G; and when G is N, then A is N orCR¹⁴ and the floating double bond is attached to A;

W is O; S; NH; N(C₁ -C₆ alkyl); or NO(C₁ -C₆ alkyl);

X is OR¹ ; S(O)_(m) R¹ ; or halogen;

R¹ is C₁ -C₆ alkyl; C₁ -C₆ haloalkyl; C₂ -C₆ alkenyl; C₂ -C₆haloalkenyl; C₂ -C₆ alkynyl; C₂ -C₆ haloalkynyl; C₃ -C₆ cycloalkyl; C₂-C₄ alkylcarbonyl; or C₂ -C₄ alkoxycarbonyl;

R² is H; C₁ -C₆ alkyl; C₁ -C₆ haloalkyl; C₂ -C₆ alkenyl; C₂ -C₆haloalkenyl; C₂ -C₆ alkynyl; C₂ -C₆ haloalkynyl; C₃ -C₆ cycloalkyl; C₂-C₄ alkylcarbonyl; C₂ -C₄ alkoxycarbonyl; hydroxy; C₁ -C₂ alkoxy; oracetyloxy;

R³ and R⁴ are each independently halogen; cyano; nitro; hydroxy; C₁ -C₆alkyl; C₁ -C₆ haloalkyl; C₂ -C₆ alkenyl; C₂ -C₆ haloalkenyl; C₂ -C₆alkynyl; C₂ -C₆ haloalkynyl; C₁ -C₆ alkoxy; C₁ -C₆ haloalkoxy; C₂ -C₆alkenyloxy; C₂ -C₆ alkynyloxy; C₁ -C₆ alkylthio; C₁ -C₆ alkylsulfinyl;C₁ -C₆ alkylsulfonyl; formyl; C₂ -C₆ alkylcarbonyl; C₂ -C₆alkoxycarbonyl; NH₂ C(O); (C₁ -C₄ alkyl)NHC(O); (C₁ -C₄ alkyl)₂ NC(O);Si(R²⁵)₃ ; Ge(R²⁵)₃ ; (R²⁵)₃ Si--C.tbd.C--; or phenyl, phenylethynyl,benzoyl, or phenylsulfonyl each substituted with R⁸ and optionallysubstituted with one or more R¹⁰ ;

R⁵ is H; C₁ -C₆ alkyl; C₁ -C₆ haloalkyl; C₂ -C₆ alkenyl; C₂ -C₆haloalkenyl; C₂ -C₆ alkynyl; C₂ -C₆ haloalkynyl; C₃ -C₆ cycloalkyl; C₂-C₄ alkylcarbonyl; or C₂ -C₄ alkoxycarbonyl;

Y is --O--; --S(O)_(n) --; --NR¹⁵ --; --C(═O)--; --CH(OR¹⁵)--; --CHR⁶--; --CHR⁶ CHR⁶ --; --CR⁶ ═CR⁶ --; --C.tbd.C--; --CHR¹⁵ O--; --OCHR¹⁵--; --CHR¹⁵ S(O)_(n) --; --S(O)_(n) CHR¹⁵ --; --CHR¹⁵ O--N═C(R⁷)--;--(R⁷)C═N--OCH(R¹⁵)--; --C(R⁷)═N--O--; --O--N═C(R⁷)--; --CHR¹⁵OC(═O)N(R¹⁵)--; --CHR¹⁵ OC(═S)N(R¹⁵)--; --CHR¹⁵ OC(═O)O--; --CHR¹⁵OC(═S)O--; --CHR¹⁵ OC(═O)S--; --CHR¹⁵ OC(═S)S--; --CHR¹⁵ SC(═O)N(R¹⁵)--;--CHR¹⁵ SC(═S)N(R¹⁵)--; --CHR¹⁵ SC(═O)O--; --CHR¹⁵ SC(═S)O--; --CHR¹⁵SC(═O)S--; --CHR¹⁵ SC(═S)S--; --CHR¹⁵ SC(═NR¹⁵)S--; --CHR¹⁵N(R¹⁵)C(═O)N(R¹⁵)--; --CHR¹⁵ O--N(R¹⁵)C(═O)N(R¹⁵)--; --CHR¹⁵O--N(R¹⁵)C(═S)N(R¹⁵)--; --CHR¹⁵ O--N═C(R⁷)NR¹⁵ --; --CHR¹⁵O--N═C(R⁷)OCH₂ --; --CHR¹⁵ O--N═C(R⁷)--N═N--; --CHR¹⁵O--N═C(R⁷)--C(═O)--; --CHR¹⁵ O--N═C(R⁷)--C(═N--A² --Z¹)--A¹ --; --CHR¹⁵O--N═C(R⁷)--C(R⁷)═N--A² --A³ --; --CHR¹⁵ O--N═C(--C(R⁷)═N--A² --Z¹)--;--CHR¹⁵ O--N═C(R⁷)--CH₂ O--; --CHR¹⁵ O--N═C(R⁷)--CH₂ S--; --O--CH₂ CH₂O--N═C(R⁷)--; --CHR¹⁵ O--C(R¹⁵)═C(R⁷)--; --CHR¹⁵ O--C(R⁷)═N--; --CHR¹⁵S--C(R⁷)═N--; --C(R⁷)═N--NR¹⁵ --; --CH═N--N═C(R⁷)--; --CHR¹⁵N(R¹⁵)--N═C(R⁷)--; --CHR¹⁵ N(COCH₃)--N═C(R⁷)--; --OC(═S)NR¹⁵ C(═O)--;--CHR⁶ --C(═W¹)--A¹ --; --CHR⁶ CHR⁶ --C(═W¹)--A¹ --; --CR⁶ ═CR⁶--C(═W¹)--A¹ --; --C.tbd.C--C(═W¹)--A¹ --; --N═CR⁶ --C(═W¹)--A¹ --; or adirect bond; and the directionality of the Y linkage is defined suchthat the moiety depicted on the left side of the linkage is bonded to Eand the moiety on the right side of the linkage is bonded to Z;

Z¹ is H or --A³ --Z;

W¹ is O or S;

A¹ is O; S; NR¹⁵ ; or a direct bond;

A² is O; NR¹⁵ ; or a direct bond;

A³ is --C(═O)--; --S(O)₂ --; or a direct bond;

each R⁶ is independently H; 1-2 CH₃ ; C₂ -C₃ alkyl; C₁ -C₃ alkoxy; C₃-C₆ cycloalkyl; formylarnino; C₂ -C₄ alkylcarbonylamino; C₂ -C₄alkoxycarbonylamino; NH₂ C(O)NH; (C₁ -C₃ alkyl)NHC(O)NH; (C₁ -C₃ alkyl)₂NC(O)NH; N(C₁ -C₃ alkyl)₂ ; piperidinyl; morpholinyl; 1-2 halogen;cyano; or nitro;

each R⁷ is independently H; C₁ -C₆ alkyl; C₁ -C₆ haloalkyl; C₁ -C₆alkoxy; C₁ -C₆ haloalkoxy; C₁ -C₆ alkylthio; C₁ -C₆ alkylsulfinyl; C₁-C₆ alkylsulfonyl; C₁ -C₆ haloalkylthio; C₁ -C₆ haloalkylsulfinyl; C₁-C₆ haloalkylsulfonyl; C₂ -C₆ alkenyl; C₂ -C₆ haloalkenyl; C₂ -C₆alkynyl; C₂ -C₆ haloalkynyl; C₃ -C₆ cycloalkyl; C₂ -C₄ alkylcarbonyl; C₂-C₄ alkoxycarbonyl; halogen; cyano; nitro; hydroxy; amino; NH(C₁ -C₆alkyl); N(C₁ -C₆ alkyl)₂ ; or morpholinyl;

each Z is independently selected from:

i) C₁ -C₁₀ alkyl, C₂ -C₁₀ alkenyl, and C₂ -C₁₀ alkynyl each substitutedwith R⁹ and optionally substituted with one or more R¹⁰ ;

ii) C₃ -C₈ cycloalkyl, C₃ -C₈ cycloalkenyl and phenyl each substitutedwith R⁹ and optionally substituted with one or more R¹⁰ ;

iii) a ring system selected from 3 to 14-membered monocyclic, fusedbicyclic and fused tricyclic nonaromatic heterocyclic ring systems and 5to 14-membered monocyclic, fused bicyclic and fused tricyclic aromaticheterocyclic ring systems, each heterocyclic ring system containing 1 to6 heteroatoms independently selected from the group nitrogen, oxygen,and sulfur, provided that each heterocyclic ring system contains no morethan 4 nitrogens, no more than 2 oxygens, and no more than 2 sulfurs,each nonaromatic or aromatic heterocyclic ring system substituted withR⁹ and optionally substituted with one or more R¹⁰ ;

iv) a multicyclic ring system selected from 8 to 14memberedfused-bicyclic and fused-tricyclic ring systems which are an aromaticcarbocyclic ring system, a nonaromatic carbocyclic ring system, or aring system containing one or two nonaromatic rings that each includeone or two Q as ring members and one or two ring members independentlyselected from C(═O) and S(O)₂, and any remaining rings as aromaticcarbocyclic rings, each multicyclic ring system substituted with R⁹ andoptionally substituted with one or more R¹⁰ ; and

v) adamantyl substituted with R⁹ and optionally substituted with one ormore R¹⁰ ;

each Q is independently selected from the group --CHR¹³ --, --NR¹³ --,--O--, and --S(O)_(p) --;

R⁸ is H; 1-2 halogen; C₁ -C₆ alkyl; C₁ -C₆ haloalkyl; C₁ -C₆ alkoxy; C₁-C₆ haloalkoxy; C₂ -C₆ alkenyl; C₂ -C₆ haloalkenyl; C₂ -C₆ alkynyl; C₁-C₆ alkylthio; C₁ -C₆ haloalkylthio; C₁ -C₆ alkylsulfinyl; C₁ -C₆alkylsulfonyl; C₃ -C₆ cycloalkyl; C₃ -C₆ alkenyloxy; CO₂ (C₁ -C₆ alkyl);NH(C₁ -C₆ alkyl); N(C₁ -C₆ alkyl)₂ ; cyano; nitro; SiR¹⁹ R²⁰ R²¹ ; orGeR¹⁹ R²⁰ R²¹ ;

R⁹ is H; 1-2 halogen; C₁ -C₆ alkyl; C₁ -C₆ haloalkyl; C₁ -C₆ alkoxy; C₁-C₆ haloalkoxy; C₂ -C₆ alkenyl; C₂ -C₆ haloalkenyl; C₂ -C₆ alkynyl; C₁-C₆ alkylthio; C₁ -C₆ haloalkylthio; C₁ -C₆ alkylsulfinyl; C₁ -C₆alkylsulfonyl; C₃ -C₆ cycloalkyl; C₃ -C₆ alkenyloxy; CO₂ (C₁ -C₆ alkyl);NH(C₁ -C₆ alkyl); N(C₁ -C₆ alkyl)₂ ; --C(R¹⁸)═NOR¹⁷ ; cyano; nitro; SF₅; SiR²² R²³ R²⁴ ; or GeR²² R²³ R²⁴ ; or R⁹ is phenyl, benzyl, benzoyl,phenoxy, pyridinyl, pyridinyloxy, thienyl, thienyloxy, furanyl,pyrimidinyl, or pyrimidinyloxy each optionally substituted with one ofR¹¹, R¹², or both R¹¹ and R¹² ;

each R¹⁰ is independently halogen; C₁ -C₄ alkyl; C₁ -C₄ haloalkyl; C₁-C₄ alkoxy; nitro; or cyano; or

when R⁹ and an R¹⁰ are attached to adjacent atoms on Z, R⁹ and saidadjacently attached R¹⁰ can be taken together as --OCH₂ O-- or --OCH₂CH₂ O--; each CH₂ group of said taken together R⁹ and R¹⁰ optionallysubstituted with 1-2 halogen; or

when Y and an R¹⁰ are attached to adjacent atoms on Z and Y is --CHR¹⁵O--N═C(R⁷)--, --O--N═C(R⁷)--, --O--CH₂ CH₂ O--N═C(R⁷)--, --CHR¹⁵O--C(R¹⁵)═C(R⁷)--, --CH═N--N═C(R⁷)--, --CHR¹⁵ N(R¹⁵)--N═C(R⁷)-- or--CHR¹⁵ N(COCH₃)--N═C(R⁷)--, R⁷ and said adjacently attached R¹⁰ can betaken together as --(CH₂)_(r) -J- such that J is attached to Z;

J is --CH₂ --; --CH₂ CH₂ --; --OCH₂ --; --CH₂ O--; --SCH₂ --; --CH₂ S--;--N(R¹⁶)CH₂ --; or --CH₂ N(R¹⁶)--; each CH₂ group of said J optionallysubstituted with 1 to 2 CH₃ ;

R¹¹ and R¹² are each independently halogen; C₁ -C₄ alkyl; C₁ -C₄haloalkyl; C₁ -C₄ alkoxy; C₁ -C₄ haloalkoxy; nitro; cyano; Si(R²⁵)₃ ; orGe(R²⁵)₃ ;

each R¹³ is independently H; C₁ -C₆ alkyl; C₁ -C₆ haloalkyl; or phenyloptionally substituted with halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁-C₄ alkoxy, C₁ -C₄ haloalkoxy, nitro or cyano;

R¹⁴ is H; halogen; C₁ -C₆ alkyl; C₁ -C₆ haloalkyl; C₂ -C₆ alkenyl; C₂-C₆ haloalkenyl; C₂ -C₆ alkynyl; C₂ -C₆ haloalkynyl; or C₃ -C₆cycloalkyl;

each R¹⁵ is independently H; C₁ -C₃ alkyl; C₃ -C₆ cycloalkyl; or phenylor benzyl, each optionally substituted on the phenyl ring with halogen,C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, nitroor cyano; or

when Y is --CHR¹⁵ N(R¹⁵)C(═O)N(R¹⁵)--, the two R¹⁵ attached to nitrogenatoms on said group can be taken together as --(CH₂)_(s) --; or

when Y is --CHR¹⁵ O--N═C(R⁷)NR¹⁵ --, R⁷ and the adjacently attached R¹⁵can be taken together as --CH₂ --(CH₂)_(s) --; --O--(CH₂)_(s) --;--S--(CH₂)_(s) --; or --N(C₁ -C₃ alkyl)--(CH₂)_(s) --; with thedirectionality of said linkage defined such that the moiety depicted onthe left side of the linkage is bonded to the carbon and the moiety onthe right side of the linkage is bonded to the nitrogen;

R¹⁶, R¹⁷, and R¹⁸ are each independently H; C₁ -C₃ alkyl; C₃ -C₆cycloalkyl; or phenyl optionally substituted with halogen, C₁ -C₄ alkyl,C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, nitro or cyano;

R¹⁹, R²⁰, R²¹, R²², R²³, and R²⁴ are each independently C₁ -C₆ alkyl; C₂-C₆ alkenyl; C₁ -C₄ alkoxy; or phenyl;

each R²⁵ is independently C₁ -C₄ alkyl; C₁ -C₄ haloalkyl; C₂ -C₄alkenyl; C₁ -C₄ alkoxy; or phenyl;

m, n and p are each independently 0, 1 or 2;

r is 0 or 1; and

s is 2 or 3.

DETAILS OF THE INVENTION

In the above recitations, the term "alkyl", used either alone or incompound words such as "alkylthio" or "haloalkyl" includesstraight-chain or branched alkyl, such as, methyl, ethyl, n-propyl,i-propyl, or the different butyl, pentyl or hexyl isomers. The term "1-2CH₃ " indicates that the substituent can be methyl or, when there is ahydrogen attached to the same atom, the substituent and said hydrogencan both be methyl. "Alkenyl" includes straight-chain or branchedalkenes such as vinyl, 1-propenyl, 2-propenyl, and the differentbutenyl, pentenyl and hexenyl isomers. "Alkenyl" also includes polyenessuch as 1,2-propadienyl and 2,4-hexadienyl. "Alkynyl" includesstraight-chain or branched alkynes such as ethynyl, 1-propynyl,2-propynyl and the different butynyl, pentynyl and hexynyl isomers."Alkynyl" can also include moieties comprised of multiple triple bondssuch as 2,5-hexadiynyl. "Alkoxy" includes, for example, methoxy, ethoxy,n-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxyisomers. "Alkenyloxy" includes straight-chain or branched alkenyloxymoieties. Examples of "alkenyloxy" include H₂ C═CHCH₂ O, (CH₃)₂ C═CHCH₂O, (CH₃)CH═CHCH₂ O, (CH₃)CH═C(CH₃)CH₂ O and CH₂ ═CHCH₂ CH₂ O."Alkynyloxy" includes straight-chain or branched alkynyloxy moieties.Examples of "alkynyloxy" include HC.tbd.CCH₂ O, CH₃ C.tbd.CCH₂ O and CH₃C.tbd.CCH₂ CH₂ O. "Alkylthio" includes branched or straight-chainalkylthio moieties such as methylthio, ethylthio, and the differentpropylthio, butylthio, pentylthio and hexylthio isomers. "Alkylsulfinyl"includes both enantiomers of an alkylsulfinyl group. Examples of"alkylsulfinyl" include CH₃ S(O), CH₃ CH₂ S(O), CH₃ CH₂ CH₂ S(O), (CH₃)₂CHS(O) and the different butylsulfmyl, pentylsulfmyl and hexylsulfinylisomers. Examples of "alkylsulfonyr" include CH₃ S(O)₂, CH₃ CH₂ S(O)₂,CH₃ CH₂ CH₂ S(O)₂, (CH₃)₂ CHS(O)₂ and the different butylsulfonyl,pentylsulfonyl and hexylsulfonyl isomers. "Cycloalkyl" includes, forexample, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl."Cycloalkenyl" includes groups such as cyclopentenyl and cyclohexenyl aswell as groups with more than one double bond such as 1,3- and1,4-cyclohexadienyl. The term "aromatic carbocyclic ring system"includes fully aromatic carbocycles and carbocycles in which at leastone ring of a polycyclic ring system is aromatic (where aromaticindicates that the Huckel rule is satisfied). The term "nonaromaticcarbocyclic ring system" denotes fully saturated carbocycles as well aspartially or fully unsaturated carbocycles where the Huckel rule is notsatisfied by any of the rings in the ring system. The term "aromaticheterocyclic ring system" includes fully aromatic heterocycles andheterocycles in which at least one ring of a polycyclic ring system isaromatic (where aromatic indicates that the Huckel rule is satisfied).The term "nonaromatic heterocyclic ring system" denotes fully saturatedheterocycles as well as partially or fully unsaturated heterocycleswhere the Huckel rule is not satisfied by any of the rings in the ringsystem. The heterocyclic ring systems can be attached through anyavailable carbon or nitrogen by replacement of a hydrogen on said carbonor nitrogen. One skilled in the art will appreciate that not allnitrogen containing heterocycles can form N-oxides since the nitrogenrequires an available lone pair for oxidation to the oxide; one skilledin the art will recognize those nitrogen containing heterocycles whichcan form N-oxides.

The term "halogen", either alone or in compound words such as"haloalkyl", includes fluorine, chlorine, bromine or iodine. The term"1-2 halogen" indicates that one or two of the available positions forthat substituent may be halogen which are independently selected.Further, when used in compound words such as "haloalkyl", said alkyl maybe partially or fully substituted with halogen atoms which may be thesame or different. Examples of "haloalkyl" include F₃ C, ClCH₂, CF₃ CH₂and CF₃ CCl₂. The terms "haloalkenyl", "haloalkynyl", "haloalkoxy", andthe like, are defined analogously to the term "haloalkyl". Examples of"haloalkenyl" include (Cl)₂ C═CHCH₂ and CF₃ CH₂ CH═CHCH₂. Examples of"haloalkynyl" include HC.tbd.CCHCl, CF₃ C.tbd.C, CCl₃ C.tbd.C and FCH₂C.tbd.CCH₂. Examples of "haloalkoxy" include CF₃ O, CCl₃ CH₂ O, HCF₂ CH₂CH₂ O and CF₃ CH₂ O. Examples of "haloalkylthio" include CCl₃ S, CF₃ S,CCl₃ CH₂ S and ClCH₂ CH₂ CH₂ S. Examples of "haloalkylsulfinyl" includeCF₃ S(O), CCl₃ S(O), CF₃ CH₂ S(O) and CF₃ CF₂ S(O). Examples of"haloalkylsulfonyl" include CF₃ S(O)₂, CCl₃ S(O)₂, CF₃ CH₂ S(O)₂ and CF₃CF₂ S(O)₂.

The total number of carbon atoms in a substituent group is indicated bythe "C_(i) -C_(j) " prefix where i and j are numbers from 1 to 10. Forexample, C₁ -C₃ alkylsulfonyl designates methylsulfonyl throughpropylsulfonyl. Examples of "alkylcarbonyl" include C(O)CH₃, C(O)CH₂ CH₂CH₃ and C(O)CH(CH₃)₂. Examples of "alkoxycarbonyl" include CH₃ OC(═O),CH₃ CH₂ OC(═O), CH₃ CH₂ CH₂ OC(═O), (CH₃)₂ CHOC(═O) and the differentbutoxy- or pentoxycarbonyl isomers. In the above recitations, when acompound of Formula I is comprised of one or more heterocyclic rings,all substituents are attached to these rings through any availablecarbon or nitrogen by replacement of a hydrogen on said carbon ornitrogen.

When a group contains a substituent which can be hydrogen, for exampleR⁹ or R¹³, then, when this substituent is taken as hydrogen, it isrecognized that this is equivalent to said group being unsubstituted.

Compounds of this invention can exist as one or more stereoisomers. Thevarious stereoisomers include enantiomers, diastereomers, atropisomersand geometric isomers. One skilled in the art will appreciate that onestereoisomer may be more active and/or may exhibit beneficial effectswhen enriched relative to the other stereoisomer(s) or when separatedfrom the other stereoisomer(s). Additionally, the skilled artisan knowshow to separate, enrich, and/or to selectively prepare saidstereoisomers. Accordingly, the present invention comprises compoundsselected from Formula I, N-oxides and agriculturally suitable saltsthereof. The compounds of the invention may be present as a mixture ofstereoisomers, individual stereoisomers, or as an optically active form.

The salts of the compounds of the invention include acid-addition saltswith inorganic or organic acids such as hydrobromic, hydrochloric,nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic,malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic orvaleric acids. The salts of the compounds of the invention also includethose formed with organic bases (e.g., pyridine, ammonia, ortriethylamine) or inorganic bases (e.g., hydrides, hydroxides, orcarbonates of sodium, potassium, lithium, calcium, magnesium or barium)when the compound contains an acidic group such as a phenol.

Preferred compounds for reasons of better activity and/or ease ofsynthesis are:

Preferred 1. Compounds of Formula I above, and N-oxides andagriculturally suitable salts thereof, wherein:

E is selected from the group 1H-pyrrole-1,2-, 2,3- and 3,4-diyl; 2,3-and 3,4-furandiyl; 2,3- and 3,4-thiophenediyl; 1H-pyrazole-1,5-, 3,4-and 4,5-diyl; 1H-imidazole-1,2-, 4,5- and 1,5-diyl; 3,4- and4,5-isoxazolediyl; 4,5-oxazolediyl; 3,4- and 4,5-isothiazolediyl;4,5-thiazolediyl; 1H-1,2,3-triazole-1,5- and 4,5-diyl;2H-1,2,3-triazole-4,5-diyl; 1H-1,2,4-triazole-1,5-diyl;4H-1,2,4-triazole-3,4-diyl; 1,2,3-oxadiazole-4,5-diyl;1,2,5-oxadiazole-3,4-diyl; 1,2,3-thiadiazole-4,5-diyl;1,2,5-thiadiazole-3,4-diyl; 1H-tetrazole-1,5-diyl; 2,3- and3,4-pyridinediyl; 3,4- and 4,5-pyridazinediyl; 4,5-pyrimidinediyl;2,3-pyrazinediyl; 1,2,3-triazine-4,5-diyl; 1,2,4-triazine-5,6-diyl;1H-indole-1,4-, 1,5-, 1,6-, 1,7-, 2,4-, 2,5-, 2,6-, 2,7-, 3,4-, 3,5-,3,6-, 3,7-, 1,2-, 2,3-, 4,5-, 5,6- and 6,7-diyl; 2,4-, 2,5-, 2,6-, 2,7-,3,4-, 3,5-, 3,6-, 3,7-, 2,3-, 4,5-, 5,6- and 6,7-benzofurandiyl;benzo[b]thiophene-2,4-, 2,5-, 2,6-, 2,7-, 3,4-, 3,5-, 3,6-, 3,7-, 2,3-,4,5-, 5,6- and 6,7-diyl; 1H-indazole-1,4-, 1,5-, 1,6-, 1,7-, 3,4-, 3,5-,3,6-, 3,7-, 4,5-, 5,6- and 6,7-diyl; 1H-benzimidazole-1,4-, 1,5-, 1,6-,1,7-, 2,4-, 2,5-, 2,6-, 2,7-, 4,5-, 5,6- and 6,7-diyl;1,2-benzisoxazole-3,4-, 3,5-, 3,6-, 3,7-, 4,5-, 5,6- and 6,7-diyl; 2,4-,2,5-, 2,6-, 2,7-, 4,5-, 5,6- and 6,7-benzoxazolediyl;1,2-benzisothiazole-3,4-, 3,5-, 3,6-, 3,7-, 4,5-, 5,6- and 6,7-diyl;2,4-, 2,5-, 2,6-, 2,7-, 4,5-, 5,6- and 6,7-benzothiazolediyl; 2,5-,2,6-, 2,7-, 2,8-, 3,5-, 3,6-, 3,7-, 3,8-, 4,5-, 4,6-, 4,7-, 4,8-, 2,3-,3,4-, 5,6-, 6,7- and 7,8-quinolinediyl; 1,5-, 1,6-, 1,7-, 1,8-, 3,5-,3,6-, 3,7-, 3,8-, 4,5-, 4,6-, 4,7-, 4,8-, 3,4-, 5,6-, 6,7- and7,8-isoquinolinediyl; 3,5-, 3,6-, 3,7-, 3,8-, 4,5-, 4,6-, 4,7-, 4,8-,3,4-, 5,6-, 6,7- and 7,8-cinnolinediyl; 1,5-, 1,6-, 1,7-, 1,8-, 5,6-,6,7- and 7,8-phthalazinediyl; 2,5-, 2,6-, 2,7-, 2,8-, 4,5-, 4,6-, 4,7-,4,8-, 5,6-, 6,7- and 7,8-quinazolinediyl; 2,5-, 2,6-, 2,7-, 2,8-, 2,3-,5,6-, 6,7- and 7,8-quinoxalinediyl; 1,8,-naphthyridine-2,5-, 2,6-, 2,7-,3,5-, 3,6-, 4,5-, 2,3- and 3,4-diyl; 2,6-, 2,7-, 4,6-, 4,7-,6,7-pteridinediyl; pyrazolo[5,1-b]thiazole-2,6-, 2,7-, 3,6-, 3,7-, 2,3-and 6,7-diyl; thiazolo[2,3-c]-1,2,4-triazole-2,5-, 2,6-, 5,6-diyl;2-oxo-1,3-benzodioxole-4,5- and 5,6-diyl; 1,3-dioxo-1H-isoindole-2,4-,2,5-, 4,5- and 5,6-diyl; 2-oxo-2H-1-benzopyran-3,5-, 3,6-, 3,7-, 3,8-,4,5-, 4,6-, 4,7-, 4,8-, 5,6-, 6,7- and 7,8-diyl;[1,2,4]triazolo[1,5-a]pyridine-2,5-, 2,6-, 2,7-, 2,8-, 5,6-, 6,7- and7,8-diyl; 3,4-dihydro-2,4-dioxo-2H-1,3-benzoxazine-3,5-, 3,6-, 3,7-,3,8-, 5,6-, 6,7- and 7,8-diyl; 2,3-dihydro-2-oxo-3,4-, 3,5-, 3,6-, 3,7-,4,5-, 5,6- and 6,7-benzofurandiyl; thieno[3,2-d]thiazole-2,5-, 2,6-, and5,6-diyl; 5,6,7,8-tetrahydro-2,5-, 2,6-, 2,7-, 2,8-, 3,5-, 3,6-, 3,7-,3,8-, 4,5-, 4,6-, 4,7-, 4,8-, 2,3- and 3,4quinolinediyl;2,3-dihydro-1,1,3-trioxo-1,2-benzisothiazole-2,4-, 2,5-, 2,6-, 2,7-,4,5-, 5,6- and 6,7-diyl; 1,3-benzodioxole-2,4-, 2,5-, 4,5- and 5,6-diyl;2,3-dihydro-2,4-, 2,5-, 2,6-, 2,7-, 3,4-, 3,5-, 3,6-, 3,7-, 4,5-, 5,6-and 6,7-benzofurandiyl; 2,3-dihydro-1,4-benzodioxin-2,5-, 2,6-, 2,7-,2,8-, 5,6- and 6,7-diyl;5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-2,4-, 2,5-, 2,6-, 2,7-,2,8-, 3,4-, 3,5-, 3,6-, 3,7-, 3,8-, and 2,3-diyl; and 1,5-, 1,6-, 1,7-,1,8-, 2,6-, 2,7-, 1,2-, and 2,3-naphthalenediyl; each aromatic ringsystem optionally substituted with one of R³, R⁴, or both R³ and R⁴ ;

W is O;

R¹ is C₁ -C₃ alkyl or C₁ -C₃ haloalkyl;

R² is H; C₁ -C₆ alkyl; C₁ -C₆ haloalkyl; or C₃ -C₆ cycloalkyl;

R³ and R⁴ are each independently halogen; cyano; nitro; C₁ -C₆ alkyl; C₁-C₆ haloalkyl; C₁ -C₆ alkoxy; C₁ -C₆ haloalkoxy; C₁ -C₆ alkylthio; C₁-C₆ alkylsulfonyl; C₂ -C₆ alkylcarbonyl; C₂ -C₆ alkoxycarbonyl; (C₁ -C₄alkyl)NHC(O); (C₁ -C₄ alkyl)₂ NC(O); benzoyl; or phenylsulfonyl;

Y is --O--; --CH═CH--; --C.tbd.C--; --CH₂ O--; --OCH₂ --; --CH₂ S(O)_(n)--; --CH₂ O--N═C(R⁷)--; --(R⁷)C═N--OCH(R¹⁵)--; --C(R⁷)═N--O--; --CH₂OC(O)NH--; --CH₂ S--C(R⁷)═N--; --CH═CR⁶ --C(═W¹)--A¹ --; or a directbond;

R⁷ is H; C₁ -C₆ alkyl; C₁ -C₆ haloalkyl; C₁ -C₆ alkoxy; C₁ -C₆alkylthio; C₂ -C₆ alkenyl; C₂ -C₆ alkynyl; C₃ -C₆ cycloalkyl; halogen;or cyano; or

when Y and an R¹⁰ are attached to adjacent atoms on Z and Y is --CH₂O--N═C(R⁷)--, R⁷ and said adjacently attached R¹⁰ can be taken togetheras --(CH₂)_(r) -J- such that J is attached to Z;

Z is selected from the group C₁ -C₁₀ alkyl; C₃ -C₈ cycloalkyl; phenyl;naphthalenyl; anthracenyl; phenanthrenyl; 1H-pyrrolyl; furanyl; thienyl;1H-pyrazolyl; 1H-imidazolyl; isoxazolyl; oxazolyl; isothiazolyl;thiazolyl; 1H-1,2,3-triazolyl; 2H-1,2,3-triazolyl; 1H-1,2,4-triazolyl;4H-1,2,4-triazolyl; 1,2,3-oxadiazolyl; 1,2,4-oxadiazolyl;1,2,5-oxadiazolyl; 1,3,4-oxadiazolyl; 1,2,3-thiadiazolyl;1,2,4-thiadiazolyl; 1,2,5-thiadiazolyl; 1,3,4-thiadiazolyl;1H-tetrazolyl; 2H-tetrazolyl; pyridinyl; pyridazinyl; pyrimidinyl;pyrazinyl; 1,3,5-triazinyl; 1,2,4-triazinyl; 1,2,4,5-tetrazinyl;1H-indolyl; benzofuranyl; benzo[b]thiophenyl; 1H-indazolyl;1H-benzimidazolyl; benzoxazolyl; benzothiazolyl; quinolinyl;isoquinolinyl; cinnolinyl; phthalazinyl; quinazolinyl; quinoxalinyl;1,8-naphthyridinyl; pteridinyl; 2,3-dihydro-1H-indenyl;1,2,3,4-tetrahydronaphthalenyl;6,7,8,9-tetrahydro-5H-benzocycloheptenyl;5,6,7,8,9,10-hexahydrobenzocyclooctenyl; 2,3-dihydro-3-oxobenzofuranyl;1,3-dihydro-1-oxoisobenzofiranyl; 2,3-dihydro-2-oxobenzofuranyl;3,4-dihydro-4-oxo-2H-1-benzopyranyl;3,4-dihydro-1-oxo-1H-2-benzopyranyl; 3,4dihydro-3-oxo-1H-2-benzopyranyl;3,4-dihydro-2-oxo-2H-1-benzopyranyl; 4-oxo-4H-1-benzopyranyl;2-oxo-2H-1-benzopyranyl; 2,3,4,5-tetrahydro-5-oxo-1-benzoxepinyl;2,3,4,5-tetrahydro-2-oxo-1-benzoxepinyl;2,3-dihydro-1,3-dioxo-1H-isoindolyl;1,2,3,4-tetrahydro-1,3dioxoisoquinolinyl;3,4-dhydro-2,4-dioxo-2H-1,3-benzoxazinyl; 2-oxo-1,3-benzodioxyl;2,3-dihydro-1,1,3-trioxo-1,2-benzisothiazolyl; 9H-fluorenyl; azulenyl;and thiazolo[2,3-c]-1,2,4-triazolyl; each group substituted with R⁹ andoptionally substituted with one or more R¹⁰ ;

R⁹ is H; 1-2 halogen; C₁ -C₆ alkyl; C₁ -C₆ haloalkyl; C₁ -C₆ alkoxy; C₁-C₆ haloalkoxy; C₁ -C₆ alkylthio; cyano; CO₂ (C₁ -C₆ alkyl); NH(C₁ -C₆alkyl); N(C₁ -C₆ alkyl)₂ ; SiR²² R²³ R²⁴ ; or GeR²² R²³ R²⁴ ; or R⁹ isC₃ -C₆ cycloalkyl, phenyl, phenoxy, pyridinyl, pyridinyloxy,pyrimidinyl, or pyrinidinyloxy, each optionally substituted with one ofR¹¹, R¹², or both R¹¹ and R¹² ; and

each R¹⁵ is independently H; C₁ -C₃ alkyl; or C₃ -C₆ cycloalkyl.

Preferred 2. Compounds of Preferred 1 wherein:

E is selected from the group 2,3- and 3,4-furandiyl; 2,3- and3,4-thiophenediyl; 2,3- and 3,4-pyridinediyl; 4,5-pyrimidinediyl; 2,4-,2,7-, 3,5-, 2,3-, 4,5-, 5,6- and 6,7-benzofurandiyl;benzo[b]thiophene-2,4-, 2,7-, 3,5-, 2,3-, 4,5-, 5,6- and 6,7-diyl; and1,6-, 1,7-, 1,2-, and 2,3-naphthalenediyl; each aromatic ring systemoptionally substituted with one of R³, R⁴, or both R³ and R⁴ ;

Z is selected from the group phenyl; 1,2,4-thiadiazolyl; pyridinyl;pyrimidinyl; and naphthalenyl; each group substituted with R⁹ andoptionally substituted with one or more R¹⁰ ;

R⁷ is H; C₁ -C₆ alkyl; C₁ -C₆ haloalkyl; C₁ -C₆ alkoxy; C₁ -C₆alkylthio; C₂ -C₆ alkenyl; C₂ -C₆ alkynyl; cyclopropyl; halogen; orcyano; or when Y and an R¹⁰ are attached to adjacent atoms on Z and Y is--CH₂ O--N═C(R⁷)--, R⁷ and said adjacently attached R¹⁰ can be takentogether as --(CH₂)_(r) -J- such that J is attached to Z;

J is --CH₂ -- or --CH₂ CH₂ --; and

r is 1.

Preferred 3. Compounds of Preferred 2 wherein:

A is O; N; NR⁵ ; or CR¹⁴ ;

X is OR¹ ;

R¹ is C₁ -C₃ alkyl;

R² is H or C₁ -C₂ alkyl;

Y is --O--; --CH═CH--; --CH₂ O--; --CH₂ O--N═C(R⁷)--;--(R⁷)C═N--OCH(R¹⁵)--; --CH₂ OC(═O)NH--; --CH₂ S--C(R⁷)═N--; or --CH═CR⁶--C(═W¹)--A¹ --;

R⁷ is H; C₁ -C₃ alkyl; C₁ -C₃ haloalkyl; C₁ -C₃ alkoxy; C₁ -C₃alkylthio; or cyclopropyl; and

each R¹⁵ is independently H; C₁ -C₃ alkyl; or cyclopropyl.

Preferred 4. Compounds of Preferred 3 wherein:

A is O or NR⁵ ;

G is C; and

Y is --O--; --CH₂ O--; or --CH₂ O--N═C(⁷)--.

Preferred 5. Compounds of Preferred 4 wherein:

R¹ is methyl; and

R² is methyl.

Preferred 6. Compounds of Preferred 3 wherein:

A is N or CR¹⁴ ;

G is N; and

Y is --O--; --CH₂ O--; or --CH₂ O--N═CR⁷)--.

Preferred 7. Compounds of Preferred 6 wherein:

R¹ is methyl; and

R² is methyl.

Most preferred are compounds of Preferred 3 selected from the group:

2,4-dihydro-5-methoxy-2-methyl-4-[2-[[[[1-[3-(trimethylsilyl)phenyl]ethylidene]amino]oxy]methyl]-3-thienyl]-3H-1,2,4-triazol-3-one;

2,4-dihydro-5-methoxy-2-methyl-4-[2-[[[[1-[3-(trifluoromethyl)phenyl]ethylidene]amino]oxy]methyl]-3-thienyl]-3H-1,2,4-triazol-3-one;

4-[2-[(2,5-dimethylphenoxy)methyl]-3-thienyl]-2,4-dihydro-5-methoxy-2-methyl-3H-1,2,4-triazol-3-one;

(1,1-dimethylethyl)2-chloro-3-[3-(1,5-dihydro-3-methoxy-1-methyl-5-oxo-4H-1,2,4-triazol-4-yl)-2-thienyl]-2-propenoate;

4-[2-[[[3-(4-chlorophenyl)-1,2,4-thiadiazol-5-yl]oxy]methyl]-3-thienyl]-2,4-dihydro-5-methoxy-2-methyl-3H-1,2,4-triazol-3-one;and

2,4-dihydro-5-methoxy-2-methyl-4-[2-[[[3-[4-(trifluoromethyl)phenyl]-1,2,4-thiadiazol-5-yl]oxy]methyl]-3-thienyl]-3H-1,2,4-triazol-3-one.

This invention also relates to fungicidal compositions comprisingfungicidally effective amounts of the compounds of the invention and atleast one of a surfactant, a solid diluent or a liquid diluent. Thepreferred compositions of the present invention are those which comprisethe above preferred compounds.

This invention also relates to a method for controlling plant diseasescaused by fungal plant pathogens comprising applying to the plant orportion thereof, or to the plant seed or seedling, a fungicidallyeffective amount of the compounds of the invention (e.g., as acomposition described herein). The preferred methods of use are thoseinvolving the above preferred compounds.

Of note are embodiments where E is a naphthalene ring, provided thatwhen G and Y are attached to the same ring, then G and Y are attached toadjacent ring members, the naphthalene ring optionally substituted withone of R³, R⁴, or both R³ and R⁴, provided that when G is attached tothe 1, 4, 5, or 8 position of the naphthalene ring, then Y is other than--O--, --S(O)_(n) --, --C(═O)--, --CHR⁶ --, --CHR⁶ CHR⁶ --, --CR⁶ ═CR⁶--, --C.tbd.C--, --OCHR¹⁵ --, --S(O)_(n) CHR¹⁵ -- or a direct bond;embodiments where R² is H, C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, C₂ -C₆alkenyl, C₂ -C₆ haloalkenyl, C₂ -C₆ alkynyl, C₂ -C₆ haloalkynyl, C₃ -C₆cycloalkyl, C₂ -C₄ alkylcarbonyl or C₂ -C₄ alkoxycarbonyl; embodimentswhere Y is --O--, --S(O)_(n) --, --NR¹⁵ --, --C(═O)--, --CH(OR¹⁵)--,--CHR⁶ --, --CHR⁶ CHR⁶ --, --CR⁶ ═CR⁶ --, --C.tbd.C--, --CHR¹⁵ O--,--OCHR¹⁵ --, --CHR¹⁵ S(O)_(n) --, --S(O)_(n) CHR¹⁵ --, --CHR¹⁵O--N═C(R⁷)--, --(R⁷)C═N--OCH(R¹⁵)--, --C(R⁷)═N--O--, --O--N═C(R⁷)--,--CHR¹⁵ OC(═O)N(R¹⁵)--, --CHR¹⁵ OC(═S)N(R¹⁵)--, --CHR¹⁵O--N(R¹⁵)C(═O)N(R¹⁵)--, --CHR¹⁵ O--N(R¹⁵)C(═S)N(R¹⁵)--, --CHR¹⁵O--N═C(R⁷)NR¹⁵ --, --CHR¹⁵ O--N═C(R⁷)OCH₂ --, --CHR¹⁵ O--N═C(R⁷)--N═N--,--CHR¹⁵ O--N═C(R⁷)--C(═O)--, --CHR¹⁵ S--C(R⁷)═N--, --C(R⁷)═N--NR¹⁵ --,--CH═N--N═C(R⁷)--, --CHR¹⁵ N(COCH₃)--N═C(R⁷)--, --OC(═S)NR¹⁵ C(═O)--,--CHR⁶ --C(═W¹)--A¹ --, --CHR⁶ CHR⁶ --C(═W¹)--A¹ --, --CR⁶ CR⁶--C(═W¹)--A¹ --, --C.tbd.C--C(═W¹)--A¹ --, --N═CR⁶ --C(═W¹)--A¹ -- or adirect bond; embodiments where R⁷ is H, C₁ -C₆ alkyl, C₁ -C₆ haloalkyl,C₁ -C₆ alkoxy, C₁ -C₆ haloalkoxy, C₁ -C₆ alkylthio, C₁ -C₆alkylsulfinyl, C₁ -C₆ alkylsulfonyl, C₁ -C₆ haloalkylthio, C₁ -C₆haloalkylsulfinyl, C₁ -C₆ haloalkylsulfonyl, C₂ -C₆ alkenyl, C₂ -C₆haloalkenyl, C₂ -C₆ alkynyl, C₂ -C₆ haloalkynyl, C₃ -C₆ cycloalkly, C₂-C₄ alkylcarbonyl, C₂ -C₄ alkoxycarbonyl, halogen, cyano or morpholinyl;embodiments where Z is other than C₃ -C₈ cycloalkenyl and adamantyl eachsubstituted with R⁹ and optionally substituted with one or more R¹⁰ ;embodiments where, when Y and an R¹⁰ are attached to adjacent atoms on Zand Y is --CHR¹⁵ O--N═C(R⁷)--, --O--N═C(R⁷)--, --CH═N--N═C(R⁷)-- or--CHR¹⁵ N(COCH₃)--N═C(R⁷)--, R⁷ and said adjacently attached R¹⁰ aretaken together as --(CH₂)_(r) --J-- such that J is attached to Z;embodiments where R¹⁹, R²⁰, R²¹, R²², R²³, and R²⁴ are eachindependently C₁ -C₆ alkyl, C₁ -C₄ alkoxy or phenyl; embodiments whereeach R²⁵ is independently C₁ -C₄ alkyl or phenyl; embodiments where R³and R⁴ are each independently halogen, cyano, nitro, C₁ -C₆ alkyl, C₁-C₆ haloalkyl, C₁ -C₆ alkoxy, C₁ -C₆ haloalkoxy, C₁ -C₆ alkylsulfonyl,C₂ -C₆ alkylcarbonyl, C₂ -C₆ alkoxycarbonyl, (C₁ -C₄ alkyl)NHC(O), (C₁-C₄ alkyl)₂ NC(O), benzoyl or phenylsulfonyl; and embodiments where Z isselected from the group phenyl, pyridinyl, pyrimidinyl and naphthalenyl,each group substituted with R⁹ and optionally substituted with one ormore R¹⁰.

The compounds of Formula I can be prepared by one or more of thefollowing methods and variations as described in Schemes 1-33. Thedefinitions of E, A, G, W, X, R¹ -R²⁵, Y, Z¹, W¹, A¹ -A³, Z, Q, J, m, n,p, r and s in the compounds of Formulae 1-58 below are as defined abovein the Summary of the Invention. Compounds of Formulae Ia-Io are varioussubsets of the compounds of Formula I, and all substituents for FormulaeIa-Io are as defined above for Formula I.

One skilled in the art will recognize that some compounds of Formula Ican exist in one or more tautomeric forms. For example, a compound ofFormula I wherein R² is H may exist as tautomer Ia or Ib, or both Ia andIb. The present invention comprises all tautomeric forms of compounds ofFormula I. ##STR5##

The compounds of Formula I can be prepared as described below inProcedures 1) to 5). Procedures 1) to 4) describe syntheses involvingconstruction of the amide ring after the formation of the aryl moiety(E-Y-Z). Procedure 5) describes syntheses of the aryl moiety (E-Y-Z)with the amide ring already in place.

1) Alkylation Procedures

The compounds of Formula I are prepared by treating compounds of Formula1 with an appropriate alkyl transfer reagent in an inert solvent with orwithout additional acidic or basic reagents or other reagents (Scheme1). Suitable solvents are selected from the group consisting of polaraprotic solvents such as acetonitrile, dimethylformamide or dimethylsulfoxide; ethers such as tetrahydrofuran, dimethoxyethane, or diethylether; ketones such as acetone or 2-butanone; hydrocarbons such astoluene or benzene; and halocarbons such as dichloromethane orchloroform. ##STR6##

For example, compounds of Formula I can be prepared by the action ofdiazoalkane reagents of Formula 2 such as diazomethane (U=H) ortrimethylsilyldiazomethane (U=(CH₃)₃ Si) on dicarbonyl compounds ofFormula 1 (Method 1). Use of trimethylsilyldiazomethane requires aprotic cosolvent such as methanol. For examples of these procedures, seeChem. Pharm. Bull., (1984), 32, 3759.

As indicated in Method 2, compounds of Formula I can also be prepared bycontacting carbonyl compounds of Formula I with alkyltrichloroacetimidates of Formula 3 and a Lewis acid catalyst. SuitableLewis acids include trimethylsilyl triflate and tetrafluoroboric acid.The alkyl trichloroacetimidates can be prepared from the appropriatealcohol and trichloroacetonitrile as described in the literature (J.Danklmaier and H. Honig, Synth. Commun., (1990), 20, 203).

Compounds of Formula I can also be prepared from compounds of Formula 1by treatment with a trialkyloxonium tetrafluoroborate (i.e., Meerwein'ssalt) of Formula 4 (Method 3). The use of trialkyloxonium salts aspowerful alkylating agents is well known in the art (see U. Schobllkopf,U. Groth, C. Deng, Angew. Chem., Int. Ed. Engl., (1981), 20, 798).

Other alkylating agents which can convert carbonyl compounds of Formula1 to compounds of Formula I are dialkyl sulfates such as dimethylsulfate, haloalkyl sulfonates such as methyl trifluoromethanesulfonate,and alkyl halides such as iodomethane and propargyl bromide (Method 4).These alkylations can be conducted with or without additional base.Appropriate bases include alkali metal alkoxides such as potassiumtert-butoxide, inorganic bases such as sodium hydride and potassiumcarbonate, or tertiary amines such as triethylamine, pyridine,1,8-diazabicyclo[5.4.0]undec-7ene (DBU), and triethylenediamine. See R.E. Benson, T. L. Cairns, J. Am. Chem. Soc., (1948), 70, 2115 foralkylation examples using agents of this type.

Compounds of Formula 1a (compounds of Formula 1 wherein G=C, W=O andX=OH) can be prepared by condensation of malonates or malonatederivatives of Formula 5 with an ambident nucleophile of Formula 6(Scheme 2). The nucleophiles of Formula 6 are N-substitutedhydroxylamines (HO--NHR²) and substituted hydrazines (HN(R⁵)--NHR²).Examples of such nucleophiles are N-methylhydroxylamine andmethylhydrazine. The malonate esters of Formula 5 can be prepared bymethods described hereinafter. The esters of Formula 5 can also beactivated by first hydrolyzing the ester to form the correspondingcarboxylic acid, and then converting the acid into the acid chloride(T=Cl) using thionyl chloride or oxalyl chloride, or into the acylimidazole (T=1-imidazolyl) by treating with 1,1'-carbonyldiimidazole.Compounds of Formula 1aa can be prepared by reaction of nitrile estersof Formula 5b with ambident nucleophiles of Formula 6. See M. Scobie andG. Tennant, J. Chem. Soc., Chem. Comm., (1994), 2451. Alkylation of 1aawith alkyl halides in the presence of base provides compounds of Formula1ab. Alternatively, treatment of 1aa with alkylamines or alkoxyaminesprovides compounds of Formula 1ab. ##STR7##

Esters of Formula 5a can be prepared from copper (I)-catalyzed reactionof malonate esters of Formula 7 with substituted aryl halides of Formula8 according to methods adapted from A. Osuka, T. Kobayashi and H.Suzuki, Synthesis, (1983), 67 and M. S. Malamas, T. C. Hohman, and J.Millen, J. Med. Chem., 1994, 37, 2043-2058, and illustrated in Scheme 3.Procedures to prepare compounds of Formula 8 are described below (seeScheme 32).

Malonate esters of Formula 5a can also be prepared from diestercarboxylic acids of Formula 5c after modification of the carboxylic acidfunctional group to the appropriate Y and Z group. A copper(I)-catalyzed coupling of nialonates of Formula 7 withorthobromocarboxylic acids of Formula 8a (see A. Bruggink, A. McKillop,Tetrahedron, (1975), 31, 2607) can be used to prepare compounds ofFormula 5c as shown in Scheme 3. Methods to prepare compounds of Formula8a are common in the art (see P. Beak, V. Snieckus, Acc. Chem. Res.,(1982), 15, 306 and Org. React., (1979), 26, 1 and references therein).##STR8##

Additionally, the malonate esters of Formula 5a can be prepared bytreating aryl acetic acid esters of Formula 9 with a dialkyl carbonateor alkyl chloroformate in the presence of a suitable base such as, butnot limited to, sodium metal or sodium hydride (Scheme 4). For example,see J. Am. Chem. Soc., (1928), 50, 2758. Nitrile esters of Formula 5bcan be prepared similarly from compounds of Formula 10. ##STR9##

Esters of Formula 9 can be prepared from acid-catalyzed alcoholysis ofaryl acetonitriles of Formula 10 or esterification of aryl acetic acidsof Formula 11 as illustrated in Scheme 5 (see Org. Synth., Coll. Vol. I,(1941), 270).

Additionally, esters of formula 9 can be prepared by palladium(0)-catalyzed cross coupling reaction of aryl iodides of Formula 8 witha Reformatsky reagent or an alkoxy(trialkylstannyl)acetylene followed byhydration (Scheme 5). For example, see T. Sakamnoto, A. Yasuhara, Y.Kondo, H. Yamanaka, Synlett., (1992), 502, and J. F. Fauvarque, A.Jutard, J. Organometal. Chem., (1977), 132, C17. ##STR10##

Aryl acetic acid esters of Formula 9a can also be prepared by copper(I)-catalyzed condensation of aryl halides of Formula 12 with compoundsof Formula 13 as described in EP-A-307,103 and illustrated below inScheme 6. ##STR11##

Some esters of Formula 9 (Formula 9b) can also be prepared by formingthe Y² bridge using conventional nucleophilic substitution chemistry(Scheme 7). Displacement of an appropriate leaving group (Lg) inelectrophiles of Formula 15 or 16 with a nucleophilic ester of Formula14 affords compounds of Formula 9b. A base, for example sodium hydride,is used to generate the corresponding alkoxide or thioalkoxide of thecompound of Formula 14. ##STR12##

Some esters of Formula 9 (Formula 9e) can also be prepared by formingthe Y³ bridge from substituted hydroxylamine 9d and carbonyl compounds14a. The hydroxylamine 9d is in turn prepared from esters 9c. Thismethod has been described in EP-A-600,835 and illustrated in Scheme 8.##STR13## 2) Displacement and Conjugate Addition/Elimination Procedures

Compounds of Formula I can also be prepared by reaction of Formula 17compounds with alkali metal alkoxides (R¹ O⁻ M⁺) or alkali metalthioalkoxides (R¹ S⁻ M⁺) in a suitable solvent (Scheme 9). The leavinggroup Lg¹ in the amides of Formula 17 are any group known in the art toundergo a displacement reaction of this type. Examples of suitableleaving groups include chlorine, bromine, and sulfonyl and sulfonategroups. Examples of suitable inert solvents are dimethylforrnamide ordimethyl sulfoxide. ##STR14##

Compounds of Formula 17a can be prepared from compounds of Formula 1b(compounds of Formula 1 wherein X is OH) by reaction with halogenatingagents such as thionyl chloride or phosphorus oxybromide to form thecorresponding β-halo-substituted derivatives (Scheme 10). Alternatively,compounds of Formula 1b can be treated with an alkylsulfonyl halide orhaloalkylsulfonyl anhydride, such as methanesulfonyl chloride,p-toluenesulfonyl chloride, and trifluoromethanesulfonyl anhydride, toform the corresponding β-alkylsulfonate of Formula 17a. The reactionwith the sulfonyl halides may be performed in the presence of a suitablebase (e.g., triethylamine). ##STR15##

As illustrated in Scheme 11, sulfonyl compounds of Formula 17b can beprepared by oxidation of the corresponding thio compound of Formula 18using well-known methods for the oxidation of sulfur (see Schrenk, K. InThe Chemistry of Sulphones and Sulphoxides; Patai, S. et al., Eds.;Wiley: New York, 1988). Suitable oxidizing reagents includemeta-chloro-peroxybenzoic acid, hydrogen peroxide and Oxone® (KHSO₅).##STR16##

Alternatively, halo-compounds of Formula 17c (compounds of Formula 17awherein A=N, G=N, and W=O) can be prepared from hydrazides of Formula 19as illustrated in Scheme 12. When R²⁷ =C(═S)S(C₁ -C₄ alkyl), the diacylcompound of Formula 19 is treated with excess thionyl halide, forexample excess thionyl chloride. The product formed first is thering-closed compound of Formula 20 which can be isolated or converted insitu to the compound of Formula 17c; see P. Molina, A. Tarraga, A.Espinosa, Synthesis, (1989), 923 for a description of this process.

Alternatively, when R²⁷ =R² as defined above, the hydrazide of Formula19 is cyclized with phosgene to form the cyclic urea of Formula 17cwherein hal=Cl. This procedure is described in detail in J. Org. Chem.,(1989), 54, 1048. ##STR17##

The hydrazides of Formula 19 can be prepared as illustrated in Scheme13. Condensation of the isocyanate of Formula 21 with the hydrazine ofFormula H₂ NNR² R²⁷ in an inert solvent such as tetrahydrofuran affordsthe hydrazide. ##STR18## 3) Conjugate Addition/Cyclization Procedures

In addition to the methods disclosed above, compounds of Formula Iwherein X=SR¹ and G=C (Formula Ic) can be prepared by treating aketenedithioacetal of Formula 22 with an ambident nucleophile of Formula6 (Scheme 14). The nucleophiles of Formula 6 are described above.##STR19##

Ketene dithioacetals of Formula 22a or 22b can be prepared by condensingaryl acetic esters of Formula 9 or amides of Formula 9a, respectively,with carbon disulfide in the presence of a suitable base, followed byreaction with two equivalents of an R¹ -halide, such as iodomethane orpropargyl bromide (Scheme 15). Conversion of 22b to 22c can beaccomplished by reaction with trialkyl tetrafluoroborates. ##STR20##

Compounds of Formula 1d (compounds of Formula 1 wherein A=N, G=N) can beprepared by condensation of N-amino-ureas of Formula 23 with acarbonylating agent of Formula 24 (Scheme 16). The carbonylating agentsof Formula 24 are carbonyl or thiocarbonyl transfer reagents such asphosgene, thiophosgene, diphosgene (ClC(═O)OCCl₃), triphosgene (Cl₃COC(═O)OCCl₃), N,N'-carbonyldiimidazole, N,N'-thiocarbonyldiimidazole,and 1,1'-carbonyldi(1,2,4-triazole). Alternatively, the compounds ofFormula 24 can be alkyl chloroformates or dialkyl carbonates. Some ofthese carbonylating reactions may require the addition of a base toeffect reaction. Appropriate bases include alkali metal alkoxides suchas potassium tert-butoxide, inorganic bases such as sodium hydride andpotassium carbonate, tertiary amines such as triethylamine andtriethylenediamine, pyridine, or 1,8-diazabicyclo[5.4.0]undec-7-ene(DBU). Suitable solvents include polar aprotic solvents such asacetonitrile, dimethylformamide, or dimethyl sulfoxide; ethers such astetrahydrofuran, dimethoxyethane, or diethyl ether; ketones such asacetone or 2-butanone; hydrocarbons such as toluene or benzene; orhalocarbons such as dichloromethane or chloroform. The reactiontemperature can vary between 0° C. and 150° C. and the reaction time canbe from 1 to 72 hours depending on the choice of base, solvent,temperature, and substrates. ##STR21##

N-Amino-ureas of Formula 23 can be prepared as illustrated in Scheme 17.Treatment of an arylamine of Formula 25 with phosgene, thiophosgene,N,N'-carbonyldiimidazole, or N,N'-thiocarbonyldimidazole produces theisocyanate or isothiocyanate of Formula 26. A base can be added forreactions with phosgene or thiophosgene. Isocyanates of Formula 26 canalso be prepared by heating acylazides of Formula 25a in a solvent suchas toluene or benzene (Curtius rearrangement). The correspondingacylazides can be prepared from well known methods in the art (seeMarch, J., Advanced Organic Chemistry; 3rd Edition, John Wiley: NewYork, (1985), pp 428, 637 and also Chem. Pharm. Bull (1977), 25, 165,and references therein. Subsequent treatment of the iso(thio)cyanatewith an R² -substituted hydrazine produces the N-amino-urea of Formula23. ##STR22##

Compounds of Formula 1e (compounds of Formula 1 wherein A=CR⁵, G=N. andX=O) can be prepared by either method illustrated in Scheme 18. Ureas ofFormula 27 are reacted with activated 2-halocarboxylic acid derivativessuch as 2-halocarboxylic acid chlorides, 2-halocarboxylic acid esters or2-haloacyl imidazoles. The initial acylation on the arylamino nitrogenis followed by an intramolecular displacement of the 2-halo group toeffect cyclization. Base may be added to accelerate the acylation and/orthe subsequent cyclization. Suitable bases include triethylamine andsodium hydride. Alternatively, Formula 1e compounds can be prepared byreaction of Formula 26 iso(thio)cyanates or Formula 26a carbodiimideswith Formula 28a esters. As described above, base may be added toaccelerate the reaction and subsequent cyclization to Formula 1ecompounds. Carbodiimides 26a can be prepared as shown in Scheme 18,starting with compounds of Formula 26. ##STR23##

The (thio)ureas or amidines of Formula 27 can be prepared by either ofthe methods illustrated in Scheme 19. The arylamine of Formula 25 can becontacted with an isocyanate or isothiocyanate of Formula R² N=C=W asdescribed above. Alternatively, an iso(thio)cyanate of Formula 26 orcarbodiimide of Formula 26a can be condensed with an amine of Formula R²--NH₂ to form the urea or amidine. The arylamine and iso(thio)cyanatesof Formulae 25 and 26, respectively, are commercially available orprepared by well-known methods. For example, isothiocyanates can beprepared by methods described in J. Heterocycl Chem., (1990), 27, 407.Isocyanates can be prepared as described in March, J., Advanced OrganicChemistry; 3rd ed., John Wiley: New York, (1985), pp 944, 1166 and alsoin Synthetic Communications, (1993), 23 (3), 335 and references therein.For methods describing the preparation of arylamines of Formula 25 thatare not commercially available, see M. S. Gibson, In The Chemistry ofthe Amino Group; Patai, S., Ed.; Interscience Publishers, 1968; p 37 andTetrahedron Lett. (1982), 23 (7), 699 and references therein. ##STR24##4) Thionation Procedures

Compounds of Formula Ie, compounds of Formula I wherein W=S, can beprepared by treating compounds of Formula Id (I wherein W=O) withthionating reagents such as P₂ S₅ or Lawesson's reagent(2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide) asillustrated in Scheme 20 (see Bull. Soc. Chim. Belg., (1978), 87, 229;and Tetrahedron Lett., (1983), 24, 3815). ##STR25##

Reaction of compounds of Formula Iea with an alkyl halide in thepresence of base provides compounds of Formula Ieb, which can be reactedwith compounds of Formula T⁵ NH₂ and then alkylated with R² --(Br, Cl,or I) to provide compounds of Formula Iec. ##STR26## 5) Aryl Moiety(E-Y-Z) Synthesis Procedures

Compounds of Formula If (compounds of Formula I wherein Y is CHR¹⁵ O,CHR¹⁵ S, or CHR¹⁵ O--N═CR⁷) can be prepared by contacting halides ofFormula 29 with various nucleophiles (Scheme 21). The appropriatealcohol or thiol is treated with a base, for example sodium hydride, toform the corresponding alkoxide or thioalkoxide which acts as thenucleophile. ##STR27##

Some aryl halides of Formula 29 can be prepared by radical halogenationof the corresponding alkyl compound (i.e., H instead of halogen inFormula 29), or by acidic cleavage of the corresponding methyl ether(i.e., OMe instead of halogen in Formula 29). Other aryl halides ofFormula 29 can be prepared from the appropriate alcohols of Formula 30by well known halogenation methods in the art (see Carey, F. A.;Sundberg, R J Advanced Organic Chemistry; 3rd ed., Part B, Plenum: NewYork, (1990), p 122).

Compounds of Formula I wherein Y is CR⁶ ═R⁶ or CHR⁶ --CHR⁶ (Formula Igand Ih, respectively) can be prepared as illustrated in Scheme 22.Treatment of the halides of Formula 29 with triphenylphosphine or atriallkylphosphite produces the corresponding phosphonium salt (Formula31) or phosphonate (Formula 32), respectively. Condensation of thephosphorus compound with a base and a carbonyl compound of FormulaZ(R⁶)C═O affords the olefin of Formula Ig. ##STR28##

The olefins of Formula Ig can be converted to the saturated compounds ofFormula Ih by hydrogenation over a metal catalyst such as palladium oncarbon as is well-known in the art (Rylander, Catalytic Hydrogenation inOrganic Synthesis; Academic: New York, 1979).

Formula Ii alkynes can be prepared by halogenation/dehalogenation ofFormula Ig olefins using procedures well-known in the art (March, J.Advanced Organic Chemistry; 3rd ed., John Wiley: New York, (1985), p924). Additionally, Formula Ii alkynes can be prepared by well-knownreaction of aryl halides with alkyne derivatives in the presence ofcatalysts such as nickel or palladium (see J. Organomet. Chem., (1975),93 253-257).

The olefin of Formula Ig can also be prepared by reversing thereactivity of the reactants in the Wittig or Horner-Emmons condensation.For example, 2-alkylaryl derivatives of Formula 33 can be converted intothe corresponding dibromo-compound of Formula 34 as illustrated inScheme 23 (see Synthesis, (1988), 330). The dibromo-compound can behydrolyzed to the carbonyl compound of Formula 35, which in turn can becondensed with a phosphorus-containing nucleophile of Formula 36 or 37to afford the olefin of Formula Ig. Carbonyl compounds of Formula 35 canalso be prepared by oxidation of halides of Formula 29 in Scheme 22 (seeTetrahedron Lett., (1990), 31, 4825 and Bull. Chem. Soc. Jpn., (1981),54, 2221 and references therein). Additionally, compounds of Formula 35can be prepared by oxidation of the corresponding alcohols of Formula30.

Vinylhalides of Formula Ij can be prepared by reacting phosphorusreagents of Formulae 37a or 37b with carbonyl compounds of Formula 35(Scheme 23). The preparations of halides of Formula 37a from theappropriate diethylphosphonoacetate are described by McKenna and Khawliin J. Org. Chem., (1986), 51, 5467. The thiono esters of Formula 37b canbe prepared from esters of Formula 37a by converting the carbonyl oxygenof the ester to a thiocarbonyl (see Chem. Rev., (1984), 84, 17 andTetrahedron Lett., (1984), 25, 2639). ##STR29##

Oximes of Formula Ik (Formula I wherein Y is C(R⁷)═N--O) can be preparedfrom carbonyl compounds of Formula 38 by condensation withhydroxylarnine, followed by O-alkylation with electrophiles of FormulaZ--(Cl, Br, or I) (Scheme 24). Alternatively, the O-substitutedhydroxylamine can be condensed with the carbonyl compound of Formula 38to yield oximes of Formula Ik directly. ##STR30##

Carbamates of Formula II can be prepared by reacting aryl alcohols ofFormula 30 with isocyanates of Formula 39 (Scheme 25). A base such astriethylamine can be added to catalyze the reaction. As shown,carbamates of Formula II can be further alkylated to provide thecarbamates of Formula Im. ##STR31##

Compounds of Formula I wherein Y is --CHR¹⁵ O--N═C(R⁷)--C(═N--A²--Z¹)--A¹ --, --CHR¹⁵ O--N═C(R⁷)--C(R⁷)═N--A² --A³ -- or --CHR.sup.15O--N═C(--C(R⁷)═N--A² --Z¹)-- can be prepared by methods known in theart or obvious modifications (see, for example, WO 95/18789, WO95/21153, and references therein) together with the methods disclosedherein.

Compounds of Formula I wherein Y is --CHR¹⁵ OC(═O)O--, --CHR¹⁵OC(═S)O--, --CHR¹⁵ OC(═O)S--, --CHR¹⁵ OC(═S)S--, --CHR¹⁵ SC(═O)N(R¹⁵)--,--CHR¹⁵ SC(═S)N(R¹⁵)--, --CHR¹⁵ SC(═O)O--, --CHR¹⁵ SC(═S)O--, --CHR¹⁵SC(═O)S--, --CHR¹⁵ SC(═S)S--, --CHR¹⁵ SC(═NR¹⁵)S-- or --CHR¹⁵N(R¹⁵)C(═O)N(R¹⁵)-- can be prepared by methods known in the art orobvious modifications (see, for example, U.S. Pat. No. 5,416,110-A, EP656351-A1 and references therein) together with the methods disclosedherein.

The compounds of the present invention are prepared by combinations ofreactions as illustrated in the Schemes 1-25 in which Z is a moiety asdescribed in the sumnmay. Preparation of the compounds containing theradical Z as described in the summnary, substituted with L (defined asany group attached to Z as depicted in each of the individual schemes)can be accomplished by one skilled in the art by the appropriatecombination of reagents and reaction sequences for a particular Z-L.Such reaction sequences can be developed based on known reactionsavailable in the chemical art. For a general reference, see March, J.Advanced Organic Chemistry; 3rd ed., John Wiley: New York, (1985) andreferences therein. See the following paragraphs for some examples ofhow L is defined in individual schemes, and the preparation ofrepresentative Z-L examples.

Compounds of Formula 41 in Scheme 26 can be prepared from compounds ofFormula 40 by reaction with hydroxylamnine or hydroxylamine salts. SeeSandler and Karo, "Organic Functional Group Preparations," Vol. 3Academic Press, New York, (1972) 372-381 for a review of methods.Compounds of Formula 41 correspond to compounds of Formula 13 in Scheme6 when Y¹ =O--N═C(R⁷) and in Scheme 21, reagent HO--N=CR⁷. ##STR32##

Compounds of Formula 40 can be prepared from compounds of Formula 39a(Scheme 27) by Friedel-Crafts acylation with compounds of Formula 42.(See Olah, G. "Friedel-Crafts and Related Reactions," Interscience, NewYork (1963-1964) for a general review). Compounds of Formula 40 may alsobe prepared by reaction of acyl halides, anhydrides, esters, or amidesof Formula 45 with organometallic reagents of Formula 44. (See March, J.Advanced Organic Chemistry; 3rd ed., John Wiley: New York, (1985), pp433-435 and references therein.) The organometallic compounds of Formula44 may be prepared by reductive metallation or halogen-metal exchange ofa halogen-containing compound of Formula 43 using, for example,magnesium or an organolithium reagent, or by deprotonation of compoundsof Formula 39a using a strong base such as a lithioamide or anorganolithium reagent, followed by transmetallation. Compound 40corresponds to Compound 14a in Scheme 8, while compound 40a correspondsto O═C(R⁶)Z in Scheme 22. ##STR33##

Compounds of Formula 43 may be prepared by reaction of compounds ofFormula 39a (Scheme 28) with, for example, bromine or chlorine, with orwithout additional catalysts, under free-radical or aromaticelectrophilic halogenation conditions, depending on the nature of Z.Alternative sources of halogen, such as N-halosuccinimides, tert-butylhypohalites or SO₂ Cl₂, may also be used. (See March, J. AdvancedOrganic Chemistry; 3rd ed., John Wiley: New York, (1985), pp 476-479,620-626, and references therein.) For a review of free-radicalhalogenation, see Huyser, in Patai,"The Chemistry of the Carbon-HalogenBond," Part 1, Wiley, New York (1973) pp 549-607. For electrophilicsubstitutions, see de la Mare, "Electrophilic Halogenation," CambridgeUniversity Press, London (1976). Compounds of Formula 43 correspond tocompounds of Formula 15 in Scheme 7 where Lg=Br, Cl, or I and reagentZ-hal in Scheme 24. Compounds of Formula 47 can be prepared fromcompounds of Formula 46 by similar procedures. Compounds of Formula 47correspond to compounds of Formula 16 in Scheme 7 where Lg=Br, Cl, or I.Compounds of Formula 36 or 37 in Scheme 23 can be prepared by reactionof compounds of Formula 47 with triphenylphosphine or trialkylphosphites, respectively, followed by deprotonation with base. SeeCadogen, "Organophosphorus Reagents in Organic Synthesis," AcademicPress, New York (1979) for a general treatise on these reagents.##STR34##

Compounds of Formula 48 can be prepared from compounds of Formula 40b bytreatment with peracids such as perbenzoic or peracetic acid, or withother peroxy compounds in the presence of an acid catalysts, followed byhydrolysis of the resultant ester. For a review, see Plesnicar, inTrahanovsky, "Oxidation in Organic Chemistry," pt. C, Academic Press,New York (1978) pp 254-267. Formula 48 corresponds to Formula 13 inScheme 6 when Y¹ =O and reagent HO-Z in Scheme 21. Compounds of Formula52 can be prepared from compounds of Formula 48 by conversion to thedialkylthiocarbamates of Formula 50 followed by rearrangement to Formula51 and subsequent hydrolysis. See M. S. Newman and H. A. Karnes, J. Org.Chem. (1966), 31, 3980-4. Formula 52 corresponds to Formula 13 in Scheme6 when Y¹ =S and reagent HS-Z in Scheme 21. ##STR35##

Compounds of Formula 53 can be converted to compounds of Formulae 43, 48or 52 via the diazonium compounds 54, by treatment with nitrous acidfollowed by subsequent reaction (Scheme 30). See reviews by Hegarty ,pt. 2, pp 511-91 and Schank, pt. 2, pp 645-657, in Patai, "The Chemistryof Diazonium and Diazo Groups," Wiley, New York (1978). Treatment ofFormula 54 compounds with cuprous halides or iodide ions yield compoundsof Formula 43. Treatment of Formula 54 compounds with cuprous oxide inthe presence of excess cupric nitrate provides compounds of Formula 48.(Cohen, Dietz, and Miser, J. Org. Chem, (1977), 42, 2053). Treatment ofFormula 54 compounds with (S₂)⁻² yields compounds of Formula 52.##STR36##

Compounds of Formula 53 can be prepared from compounds of Formula 39a bynitration, followed by reduction (Scheme 31). A wide variety ofnitrating agents is available (see Schofield, "Aromatic Nitration,"Cambridge University Press, Cambridge (1980)). Reduction of nitrocompounds can be accomplished in a number of ways (see March, J.Advanced Organic Chemistry; 3rd ed., John Wiley: New York, (1985), pp1103-4 and references therein). Formula 53 corresponds to Formula 13 inScheme 6 when Y¹ =NR¹⁵ and R¹⁵ =H. ##STR37##

Iodides of Formula 8 can be prepared from compounds of Formula 58 by themethods described above in Schemes 21-25 for various Y-Z combinations.Compounds of Formula 58 can in turn be prepared from compounds ofFormula 57 by functional group interconversions which are well known toone skilled in the art. The compounds of Formula 57 can be prepared bytreating compounds of Formula 56 with an organolithium reagent such asn-BuLi or LDA followed by trapping the intermediate with iodine (Beak,P., Snieckus, V. Acc. Chem. Res., (1982), 15,306). Additionally,lithiation via halogen metal exchange of compounds of Formula 56, whereH is replaced by Br, will produce an intermediate which can be trappedwith iodine to prepare compounds of Formula 57 (Parham, W E, Bradsher,C. K. Acc. Chem. Res., (1982), 15, 300 (Scheme 32). ##STR38##

Conversion of compounds of Formula In to compounds of Formula Io issummarized in Scheme 33. Reaction of the secondary amides withsilylating agents, such as trimethylsilyl chloride in the presence ofbase or hexamethyldisilazane in the presence of acid, provides thesilylated intermediate which is oxidized in situ with theperoxo-molybdenum compound MoO₅.HMPA complexed with pyridine ordimethylformamide. Subsequent hydrolysis with aqueous EDTA(ethylenediaminetetraacetic acid) liberates the hydroxylated armides(see S. A. Martin, P. G. Sammes and R. M. Upton, J. Chem. Soc., PerkinTrans 1, (1979), 2481 and J. H. Rigby and M. Qabar, J. Org. Chem.(1989), 54, 5852). Optional alkylation with C₁ -C₂ alkyl halides in thepresence of base or acylation with acetic anhydride can be performed onthe hydroxyl amides of Formula Io where R^(2') =OH. ##STR39##

It is recognized that some reagents and reaction conditions describedabove for preparing compounds of Formula I may not be compatible withcertain functionalities present in the intermediates. In theseinstances, the incorporation of protection/deprotection sequences orfunctional group interconversions into the synthesis will aid inobtaining the desired products. The use and choice of the protectinggroups will be apparent to one skilled in chemical synthesis (see, forexample, Greene, T. W.; Wuts, P. G. M. Protective Groups in OrganicSynthesis, 2nd ed.; Wiley: New York, 1991). One skilled in the art willrecognize that, in some cases, after the introduction of a given reagentas it is depicted in any individual scheme, it may be necessary toperform additional routine synthetic steps not described in detail tocomplete the synthesis of compounds of Formula I. One skilled in the artwill also recognize that it may be necessary to perform a combination ofthe steps illustrated in the above schemes in an order other than thatimplied by the particular sequence presented to prepare the compounds ofFormula I.

One skilled in the art will also recognize that compounds of Formula Iand the intermediates described herein can be subjected to variouselectrophilic, nucleophilic, radical, organometallic, oxidation, andreduction reactions to add substituents or modify existing substituents.

Without further elaboration, it is believed that one skilled in the artusing the preceding description can utilize the present invention to itsfullest extent. The following Examples are, therefore, to be construedas merely illustrative, and not limiting of the disclosure in any waywhatsoever. Percentages are by weight except for chromatographic solventmixtures or where otherwise indicated. Parts and percentages forchromatographic solvent mixtures are by volume unless otherwiseindicated. ¹ H NMR spectra are reported in ppm downfield fromtetramethylsilane; s=singlet, d=doublet, t=triplet, m=multiplet,dd=doublet of doublets, br s=broad singlet.

EXAMPLE 1

Step A: Preparation of methyl 3-isocyanato-2-thiophenecarboxylate

Diphosgene (4.6 mL) was added dropwise to a solution of methyl3-amino-2-thiophenecarboxylate (5.0 g) in p-dioxane (100 mL) at roomtemperature under N₂. Triethylamine (5.3 mL) was then added withconcomitant formation of a white precipitate. The resulting reactionmixture was heated at reflux overnight. The reaction was allowed to coolto room temperature and then filtered to remove solid impurities. Theprecipitate was rinsed with diethyl ether (about 250 mL) and thefiltrate was concentrated under reduced pressure to yield 6.4 g of crudetitle compound of Step A as a brown solid. ¹ H NMR (CDCl₃): δ 7.43(d,1H), 6.78 (d,1H), 3.92 (s,3H).

Step B: Preparation of methyl3-[[(2,2-dimethylhydrazino)carbonyl]amino]-2-thiopnecarboxylate

The tide compound of Step A (6.4 g) was dissolved in toluene (35 mL)under N₂ and the solution was cooled to about 5° C. (ice bath) followedby the subsequent addition of 1,1-dimethylhydrazine (2.7 mL). A beigeprecipitate formed immediately and the mixture was allowed to stir for30 min. The solid was filtered off, rinsed with hexane and then driedunder vacuum to afford 6.9 g (81%) of the title compound of Step B. ¹ HNMR (CDCl₃): δ 10.66 (br s,1H), 8.05 (d,1H), 7.43 (d,1H), 5.49 (brs,1H), 3.89 (s,3H), 2.65 (s,6H).

Step C: Preparation of methyl3-(3-chloro-4,5-dihydro-1-methyl-5-oxo-1H-1,2,4-triazol-4-yl)-2-thiophenecarboxylate

Triphosgene (16.8 g) was added to a solution of the title compound ofStep B (6.9 g) in methylene chloride (250 mL) under N₂. The reactionmixture was heated at reflux overnight, cooled, and then concentratedunder reduced pressure. The resulting brown oil was dissolved inmethylene chloride and washed with water. The aqueous layer was furtherextracted three times with methylene chloride and the combined organicextracts were dried (MgSO₄), filtered and concentrated in vacuo to yield7.92 g of the title compound of Step C. ¹ H NMR (CDCl₃): δ 7.66 (d,1H),7.13 (d,1H), 3.85 (s,3H), 3.52 (s,3H).

Step D: Preparation of methyl3-(4,5-dihydro-3-methoxy-1-methyl-5-oxo-1H-1,2,4-triazol-4-yl)-2-thiophenecarboxylate

Sodium methoxide (16.5 mL of a 30% solution in methanol) was added to asolution of the title compound of Step C (7.9 g) in anhydrousdimethoxyethane/methanol (85 mL/35 mL). The resulting yellow solutionwas heated to 50° C. for 2 h under N₂ and then left to stir overnight atroom temperature. The reaction mixture was concentrated under reducedpressure and the residue was dissolved in methylene chloride. Theresulting mixture was washed with water and then with saturated aqueousNaCl. The aqueous layer was filtered through Celite® and the filtratewas extracted three times with methylene chloride. The combinedmethylene chloride layers were dried (MgSO₄), filtered, and concentratedunder reduced pressure to give 5.4 g of an off-white solid. The crudeproduct was purified by flash chromatography (20-100% ethylacetate/hexane as eluent) to afford 3.9 g of the title compound of StepD as a white solid. ¹ H NMR (CDCl₃): δ 7.58 (d,1H), 7.12 (d,1H), 3.93(s,3H), 3.83 (s,3H), 3.44(s,3H).

Step E: Preparation of2,4-dihydro-4-[2-(hydroxymethyl)-3-thienyl]-5-methoxy-2-methyl-3H-1,2,4-triazol-3-one

To a solution of the title compound of Step D (1.8 g) in methylenechloride (23 mL) under N₂ at -78° C. was added a solution ofdiisobutylaluminum hydride (18.3 mL, 1 M) in methylene chloride. Theresulting solution was allowed to stir at -78° C. for 15 min, warmed toroom temperature and then stirred for 1.5 h. After cooling the reactionmixture to -78° C., acetone was added and after about 10 min, thereaction mixture was quenched with 1N HCl. The reaction mixture wasallowed to warm to room temperature, was diluted further with methylenechloride, and was then washed with water. The organic layer was dried(MgSO₄), filtered and concentrated in vacuo to yield 1.3 g of the titlecompound of Step E as an off-white solid.

Step F: Preparation of4-[2-(bromomethyl)-3-thienyl]-2,4-dihydro-5-methoxy-2-methyl-3H-1,2,4-triazol-3-one

To a suspension of the title compound of Step E (2.6 g) in methylenechloride (20 mL) under N₂ at room temperature was added sequentiallytriphenylphosphine (3.44 g) and carbon tetrabromide (5.58 g). Theresulting orange solution was allowed to stir for 1 h at roomtemperature and was then concentrated under reduced pressure to give anorange oil. The residue was purified by flash chromatography (1:1 ethylacetate:hexane as eluent) to afford 2.3 g of the title compound of StepF, a compound of the invention, as a white solid. ¹ H NMR (CDCl₃): δ7.34 (d,1H), 6.92 (d,1H), 4.65 (s,2H), 3.98 (s,3H), 3.45 (s,3H).

EXAMPLE 2

Step A: Preparation of 2-(3-bromophenyl)-2-methyl-1,3-dioxolane

1-(3-bromophenyl)ethanone (60.6 g), ethylene glycol (83.7 mL), andp-toluenesulfonic acid (0.15 g) were dissolved in benzene (250 mL) andheated at reflux overnight in a Dean-Stark apparatus. The mixture wascooled and washed with water. The aqueous layer was further extractedtwice with chlorobutane and the combined organic layers were dried(MgSO₄), filtered and the solvent was removed under reduced pressure toyield 75.0 g of a yellow oil. The oil was purified by distillation underreduced pressure (19-24 Pa, 64-74° C.) to afford 70.1 g of the titlecompound of Step A as an oil. ¹ H NMR (CDCl₃): δ 7.64 (s,1H), 7.40(m,2H), 7.20 (m,1H), 4.0 (m,2H), 3.7 (m,2H), 1.63 (s,3H).

Step B: Preparation of2-[3-(trimethylsilyl)phenyl]-2-methyl-1,3-dioxolane

A three-neck flask was charged with magnesium pieces (2.0 g) andtetrahydrofuiran (12 mL) under a nitrogen atmosphere. A small quantityof iodine was added and the mixture turned yellow. To this yellowmixture was added dropwise a solution of the title compound of Step A(20.0 g) in 30 mL of THF. The reaction mixture was warmed to 65° C.during the addition and then was heated at reflux for 1.5 h after theaddition was complete. After cooling the reaction to 60° C., a solutionof trimethylsilyl chloride (10.4 mL) in THF (12 mL) was added and themixture was heated at reflux for two hours and then was allowed to stirovernight at room temperature. The reaction mixture was poured intosaturated aqueous NH₄ Cl and the aqueous layer was extracted twice withdiethyl ether and then once with ethyl acetate. The combined organiclayers were dried over MgSO₄, filtered and the was solvent removed togive an oil (20.0 g) which crystallized upon standing. This solid wasthen recrystallized from pentane to afford 11.2 g of the title compoundof Step B as a white solid melting at 54-55° C. ¹ H NMR (CDCl₃): δ 7.63(s,1H), 7.44 (m,2H), 7.33 (t,1H), 4.0 (m,2H), 3.78 (m,2H), 1.67 (s,3H),0.27 (s,8H).

Step C: Preparation of 1-[3-(trimethylsilyl)phenyl]ethanone

To a solution of the title compound of Step B (11.2 g) in acetone (400mnL) was added an aqueous solution of 1N hydrochloric acid (6 mL) andthe mixture was heated at reflux overnight. After cooling, the mixturewas concentrated under reduced pressure and the resulting residue wasdissolved in diethyl ether and dried (MgSO₄). The drying agent wasremoved by filtration and the solvent was removed under reduced pressureto give a yellow oil. The crude product was combined with another batchof crude product prepared in the same manner and purified bydistillation (47 Pa, 58-59° C.) to afford 8.9 g of the title compound ofStep C as an oil. ¹ H NMR (CDCl₃): δ 8.11 (s,1H), 7.92 (d,1H), 7.7(d,1H), 7.47 (t,1H), 2.62 (s,3H), 0.30 (s,8H).

Step D: Preparation of 1-[3-(trimethylsilyl)phenyl]ethanone oxime

To a solution of the title compound of Step C (8.9 g) in methanol (120mL)/water (50 mL) was added sodium acetate (7.5 g) followed by theaddition of hydroxylamine hydrochloride (3.8 g). The mixture was heatedat reflux overnight, cooled to room temperature, and concentrated to anoil. The oil was mixed with water and extracted three times withmethylene chloride. The combined organic phases were dried (MgSO₄),concentrated, and chromatographed on silica gel with 8% ethylacetate/hexane to afford the title compound of Step D as an oil. ¹ H NMR(CDCl₃): δ 8.8 (br s,1H), 7.77 (s,1H), 7.5 (m,2H), 7.37 (t,1H), 2.31(s,3H), 0.27 (s,8H).

Step E: Preparation of2,4-dihydro-5-methoxy-2-methyl-4-[2-[[[[1-[3-(trimethylsilyl)phenyl]ethylidene]amino]oxy]methyl]-3-thienyl]-3H-1,2,4-triazol-3-one

A solution of the title compound of Step D (1.6 g) in DMF (18 mL) wascooled to 0° C. (ice bath) under N₂. Sodium hydride (236 mg) was addedand, after 20 min, a solution of the title compound of Step F in Example1 (2.3 g) in DMF (18 mL) was added. The reaction mixture was kept at 0°C. for 1 h and then at room temperature for another hour beforequenching with water. The mixture was extracted four times with ethylacetate and the combined organic extracts were washed with saturatedaqueous NaCl, dried (MgSO₄), filtered and concentrated under reducedpressure to a gold oil. The crude product was purified by flashchromatography (1:1 ethyl acetate:hexane as eluent) to afford 2.7 g ofthe title compound of Step E, a compound of the invention, as a veryviscous oil/solid. ¹ H NMR (CDCl₃): δ 7.76 (s,1H), 7.60 (m,1H), 7.54(m,1H), 7.36 (d,1H), 7.32 (d,1H), 6.94 (d,1H), 5.29 (s,2H), 3.89 (s,3H),3.41 (s,3H), 2.21 (s,3H), 0.28 (s,9H).

EXAMPLE 3

Preparation of4-[2-[(2,5-dimethylphenoxy)methyl]-3-thienyl]-2,4-dihydro-5-methoxy-2-methyl-3H-1,2,4-triazol-3-one

To a solution of the title compound of Step E in Example 1 (200 mg),2,5-dimethylphenol (152 mg) and triphenylphosphine (261 mg) in THF (2mL) at 0° C. (ice bath) under N₂ was added diethyl azodicarboxylate (231mg). The ice bath was removed and the reaction mixture warmed to roomtemperature. After stirring for 4 h at room temperature, the reactionmixture was concentrated under reduced pressure to give an orange oil.Purification of this orange oil by flash chromatography (1:1 ethylacetate:hexane eluent) followed by preparative TLC (10% ethylacetate/methylene chloride) afforded 100 mg of the title compound ofExample 3, a compound of the invention, as yellow-brown solid melting at151-153° C. ¹ H NMR (CDCl₃): δ 7.34 (d,¹ H), 7.01 (d,1H), 6.95 (d,1H),6.68 (m,2H), 5.15 (s,2H), 3.94 (s,3H), 3.43 (s,3H), 2.30 (s,3H), 2.16(s,3H).

EXAMPLE 4

Step A: Preparation of3-(1,5-dihydro-3-methoxy-1-methyl-5-oxo-4H-1,2,4-triazol-4-yl)-2-thiophenecarboxaldehyde

A solution of 4-methylmorpholine N-oxide (0.38 g, 0.0033 mol) indichloromethane (7 mL) was stirred over anhydrous magnesium sulfate for15 minutes and then filtered. Molecular sieves (4 Å) were added to thefiltrate, followed by tetrapropylamrnonium perruthenate (0.11 g, 0.0003mol). A solution of the title compound of Step E in Example 1 (0.39 g,0.0016 mol) in dichloromethane (1 mL) was added and the resultingmixture was stired at room temperature for 1 hr. The reaction mixturewas diluted with diethyl ether (10 mL), filtered through a short plug ofsilica gel, and the filtrate was concentrated by rotary evaporation togive 0.21 g of the title compound of Step A as a pale solid. ¹ H NMR(400 MHz, CDCl₃): δ 9.84 (s,1H), 7.79 (d,1H, J=5.2 Hz), 7.16 (d,1H,J=5.2 Hz), 4.01 (s,3H), 3.46 (s,3H).

Step B: Preparation of (1,1-dimethylethyl)dichloro(diethoxyphosphinyl)acetate

A solution of 5.25% sodium hypochlorite (Clorox® bleach; 421.5 g, 0.2973mol) was adjusted to pH 7.1 with 3N HCl. tert-Butyldiethylphosphonoacetate (15.0 g, 0.0595 mol) was added dropwise at 0° C.with vigorous stirring. After complete addition, the ice bath wasremoved and stirring was continued for 1 h. The reaction mixture wasextracted five times with hexane and the combined organic phases weredried (MgSO₄), filtered and concentrated to afford 18.4 g of the titlecompound of Step B as a colorless oil. ¹ H NMR (300 MHz, CDCl₃): δ4.41-4.36 (m,4H), 1.57 (s,9H), 1.40 (t,6H, J=7.2 Hz).

Step C: Preparation of (1,1-dimethylethyl)chloro(diethoxyphosphinyl)acetate

The title compound of Step B (18.4 g, 0.0572 mol) was dissolved inethanol (140 mL) and cooled to 0° C. A solution of sodium sulfite (14.4g, 0.1144 mol) in H₂ O (63 mL) was added with stirring such that theinternal temperature remained below 14° C. The cooling bath was removedand the mixture was stirred at room temperature for 30 min. The reactionmixture was extracted five times with chloroform, and the combinedorganic phase was dried (MgSO₄), filtered and concentrated to afford16.4 g of the title compound of Step C as a clear oil. ¹ H NMR (300 MHz,CDCl₃): δ 4.43 (d,1H, J=15.9 Hz), 4.30-4.24 (m,4H), 1.52 (s,9H), 1.38(t,6H, J=6.9 Hz).

Step D: Preparation of (1,1-dimethylethy)2-chloro-3-[3-(1,5-dihydro-3-methoxy-1-methyl-5-oxo-4H-1,2,4-triazol-4-yl)-2-thienyl]-2-propenoate

A solution of the title compound of Step C (0.026 g, 0.0009 mol) inethyl acetate (2 mL) was added to a mixture of calcium hydroxide (0.068g, 0.0009 mol) and the title compound of Step A (0.220 g, 0.0009 mol) inethyl acetate (5 mL). The resulting mixture was stirred at 60° C.overnight. Three additional 0.026 g (0.0009 mol) portions of the titlecompound of Step C were added at 3 h intervals and then the temperatureof the mixture was increased to 70° C. and heating was continuedovernight. After 40 h of total reaction time, the reaction mixture waspoured into ice water and extracted three times with ethyl acetate. Thecombined organic phase was washed successively with saturated aqueousNaCl and then with a 1/1 mixture of saturated aqueous NaCl and saturatedaqueous sodium hydrogen carbonate, dried (Na₂ SO₄), filtered andconcentrated to a pale yellow oil. The crude product was purified byflash column chromatography on silica gel to give a preliminary fractionof 0.170 g of the title compound of Step D, a compound of the invention,as a white solid (m.p. 105-115° C.) consisting of a 7:3 ratio of Z- andE-isomers, respectively, followed by a final fraction of 0.04 g of thetitle compound of Step D, a compound of the invention, as a white solid(m.p. 104° C.) consisting of a 5:1 ratio of Z- and E-isomers,respectively. ¹ H NMR (300 MHz, CDCl₃ : for the Z/E mixture): δ 7.77 and7.00 (2d,1H total, J=0.8 Hz), 7.62 and 7.46 (2dd,1H total, J=0.8, 5.4Hz), 7.09 and 6.98 (2dd,1H total, J=0.9, 5.4 Hz), 3.97 (s,3H), 3.45(s,3H), 1.54 (s,9H).

EXAMPLE 5

Step A: Preparation of monomethyl 3,4-furandicarboxylate

A solution of NaOH (5.0 g) in H₂ O/methanol (20 ml/60 mL) was added to asolution of dimethyl 3,4-furandicarboxylate (23 g) in methanol (250 mL)at 0° C. The mixture was allowed to stir at 0° C. for 2 h, and then waswarmed to room temperature and left to stir overnight. The congealedmixture was concentrated under reduced pressure and the resulting solidwas dissolved in water. The aqueous solution was extracted three timeswith diethyl ether and the combined organic extracts were dried (MgSO₄),filtered and concentrated under reduced pressure to afford a white solid(3.5 g) which was the starting dimethyl 3,4-furandicarboxylate. Theremaining aqueous layer was acidified by dropwise addition ofconcentrated HCl and extracted three times with methylene chloride. Thecombined methylene chloride extracts were dried (MgSO₄), filtered andconcentrated under reduced pressure to afford 22.97 g of the titlecompound of Step A as a white solid. ¹ H NMR (CDCl₃): δ 13.02 (br s,1H),8.25 (d,1H), 8.13 (d,1H), 4.00 (s,3H).

Step B: Preparation of methyl 4-(azidocarbonyl)-3-furancarboxylate

To a solution of the title compound of Step A (23 g), triethylamine(18.8 mL) and DMF (120 mL) at 0° C. under nitrogen was added a solutionof diphenylphosphorylazide (29.1 mL) in DMF (20 mL) via an additionfunnel. The reaction was allowed to stir for 3 h at 0° C. and wasmonitored by TLC (1:1 ethyl acetate/hexane). The reaction mixture waspoured onto an ice/diethyl ether mixture and then extracted three timeswith diethyl ether. The combined organic extracts were washed with a 10%aqueous NaHCO₃ solution, dried (MgSO₄) and concentrated to give 24 g ofcrude product, the title compound of Step B, as an oil/solid mixture.

Step C: Preparation of methyl4-[[(2,2-dimethylhydrazino)carbonyl]amino]-3-furancarboxylate

A solution of the title compound of Step B (24 g) in toluene (200 mL)was heated at 70° C. for 3 h and then at 90° C. for another 3 h. Thereaction was followed by IR. After cooling to 0° C.,1,1-dimethylhydrazine (9.4 mL) was added and the reaction was allowed tostir overnight at room temperature. The resulting precipitate wascollected by filtration to afford 13.5 g of the title compound of Step Cas a white solid melting at 138-139° C. The filtrate was concentratedunder reduced pressure to give a second batch, 15.7 g of crude product,the title compound of Step C, as an orange solid. ¹ H NMR (CDCl₃): δ9.28 (br s,1H), 8.03 (d,1H), 7.85 (d,1H), 5.44 (d,1H), 3.88 (s,3H), 2.62(s,6H).

Step D: Preparation of methyl4-(3-chloro-1,5-dihydro-1-methyl-5-oxo-4H-1,2,4-triazol-4-yl)-3-furancarboxylate

Triphosgene (40.1 g) was added to a solution of crude title compound ofStep C (15.4 g) in methylene chloride (550 mL) at 0° C. The mixture washeated at reflux for 4 h, cooled to room temperature and stirredovernight. The reaction mixture was concentrated to a brown oil whichwas dissolved in methylene chloride, washed with water and the aqueouslayer extracted three times with methylene chloride. The combinedorganic extracts were dried (MgSO₄), filtered and concentrated to abrown oil. Purification by flash chromatography (1:1 hexane:ethylacetate) provided 5.34 g of the title compound of Step D as a yellowsolid melting at 129-130° C. ¹ H NMR (CDCl₃): δ 8.10 (d,1H), 7.72(d,1H), 3.80 (s,3H), 3.52 (s,3H).

Step E: Preparation of methyl4-(1,5-dihydro-3-methoxy-1-methyl-5-oxo-4H-1,2,4-triazol-4-yl)-3-furancarboxylate

A solution of sodium methoxide (11.4 mL, 30% in methanol) was added to asolution of the title compound of Step D (5.34 g) inmethanol/dimethoxyethane (26 mL/26 mL) while stirring under nitrogen.The yellow solution was heated to 40° C. for 5 h, cooled to roomtemperature and left to stir overnight under nitrogen. The reactionmixture was poured into saturated aqueous NH₄ Cl (50 mL) and theresulting mixture was extracted three times with ethyl acetate. Thecombined organic extracts were dried (MgSO₄), filtered and concentratedto a yellow solid. The yellow solid was dried under vacuum to afford 4.7g of the title compound of Step E melting at 131-133° C. ¹ H NMR(CDCl₃): δ 8.04 (d,1H), 7.68 (d,1H), 3.94 (s,3H), 3.78 (s,3H), 3.43(s,3H).

Step F: Preparation of2,4-dihydro-4-[4-(hydroxymethyI)-3-furanyl]-5-methoxy-2-methyl-3H-1,2,4-triazol-3-one

A solution of the title compound of Step E (4.6 g) in methylene chloride(40 mL) under nitrogen was cooled to -78° C. while stirring. A solutionof diisobutylaluminum hydride (55.0 mL, 1 M in CH₂ Cl₂) in methylenechloride was then added, the reaction mixture was allowed to warm toroom temperature and stirred for 1 h. The reaction was monitored by TLC(5% methanol/ethyl acetate). After cooling back down to -78° C., thereaction was diluted with acetone (45 mL), quenched with glacial aceticacid (20 mL) and then allowed to warm to room temperature. The resultingmixture was further diluted with water (200 mL) and extractedsuccessively with methylene chloride and ethyl acetate. The combinedorganic extracts were dried (MgSO₄), filtered and concentrated underreduced pressure to yield 3.62 g of the title compound of Step F as anorange solid melting at 132.5-133.5° C. ¹ H NMR (CDC₃): δ 7.53 (s,2H),4.38 (s,3H), 3.99 (s,3H), 3.44 (s,3H).

Step G: Preparation of4-[4-(bromomethyl)-3-furanyl]-2,4-dihydro-5-methoxy-2-methyl-3H-1,2,4-triazol-3-one

To a solution of the title compound of Step F (3.6 g), andtriphenylphosphine (5.1 g) in methylene chloride (40 mL) under N₂ at 0°C. was added carbon tetrabromide (8.0 g). The resulting orange solutionwas allowed to stir overnight at room temperature and then wasconcentrated under reduced pressure to give a brown oil. The residue waspurified by flash chromatography (1:2 ethyl acetate:hexane as eluent) toafford 3.6 g (78%) of the title compound of Step G, a compound of theinvention, as a white solid melting at 147-149° C.

EXAMPLE 6 Preparation of2,4-dihydro-5-methoxy-2-methyl-4-[4-[[[[1-[3-(trimethylsilyl)phenyl]ethylidene]amino]oxy]methyl]-3-furanyl]-3H-1,2,4-triazol-3-one

A solution of the title compound of Step D in Example 2 (180 mg) in DMF(2 mL) under N₂ was cooled to 0° C. Sodium hydride (27 mg, 95%) wasadded and the mixture was stirred at 0° C. for 20 min. A solution of thetitle compound of Step G in Example 5 (250 mg) in DMF (2 mL) was addedvia syringe and the resulting mixture was allowed to warm to roomtemperature. The mixture was left to stir overnight at room temperature.The reaction mixture was cooled to 0° C., quenched with water andextracted three times with methylene chloride. The combined organicextracts were dried (MgSO₄), filtered and concentrated under reducedpressure to a yellow oil. The oil was purified by flash chromatography(1:2 ethyl acetate:hexane as eluent) to afford 242 mg of the tidecompound of Example 6, a compound of the invention, as a clear oil. ¹ HNMR (CDCl₃): δ 7.70 (s,1H), 7.54 (m,4H), 7.34 (t,1H), 5.11 (s,2H), 3.86(s,3H), 3.32 (s,3H), 2.14 (s,3H), 0.28 (s,9H).

EXAMPLE 7

Step A: Preparation of3,4-dihydro-7-methoxy-N-(phenylmethyl)-1-naphthalenamine

A mixture containing 7-methoxytetralone (25.0 g), benzylamine (15.8 mL),toluene and 4 Å molecular sieves (42.0 g) was heated at reflux for 3.5h. The mixture was cooled to room temperature, filtered through a layerof Florisil® and concentrated under reduced pressure to yield 42.1 g ofcrude title compound of Step A.

Step B: Preparation of 7-methoxy-1-naphthalenamine

To a solution of crude title compound of Step A (42.1 g) in diphenylether (320 mL) was added 10% palladium on carbon (17.8 g). Theheterogeneous black mixture was heated at reflux for 5 h under N₂ whilestirring. The reaction mixture was allowed to cool to room temperatureand filtered. The filtrate was acidified with concentrated HCl and theresulting white precipitate was collected by filtration, washed with CH₂Cl₂, dissolved in water and treated with 50% aqueous NaOH until basic.The aqueous mixture was then extracted four times with CH₂ Cl₂. Thecombined organic extracts were dried (MgSO₄), filtered and the filtratewas concentrated under reduced pressure to give 20.9 g of the titlecompound of Step B as a pink solid melting at 79-80° C. ¹ H NMR (CDCl₃):δ 7.70 (d,1H), 7.29-7.13 (m,3H), 7.07 (d,1H), 6.80 (dd,1H), 4.0 (brs,2H), 3.94 (s,3H).

Step C: Preparation of 1-isocyanato-7-methoxynaphthalene

To a solution of the title compound of Step B (5.0 g) in p-dioxane (115mL) at room temperature was added via syringe diphosgene (4.2 mL)followed by the addition of triethylamine (4.8 mL). The mixture washeated at reflux overnight while stirring. The reaction was monitored byIR (2267 cm⁻¹). The reaction mixture was filtered and the residue waswashed with diethyl ether. The filtrate was concentrated under reducedpressure to give 5.8 g of the title compound of Step C as a beige solidwhich was used without further purification.

Step D: Preparation ofN-(7-methoxy-1-naphthalenyl)-2,2-dimethylhydrazinecarboxamide

A solution of crude title compound of Step C (5.8 g) in toluene (85 mL)was cooled to 0° C. under N₂. While stirring the reaction solution,1,1-dimethylhydrazine (2.5 mL) was added and the mixture was allowed towarm to room temperature. After stirring for 30 min at room temperature,a precipitate formed. Filtration afforded 5.1 g of the title compound ofStep D as a white solid melting at 152-153° C. ¹ H NMR (CDCl₃): δ 8.48(br s,1H), 7.89 (d,1H), 7.77 (m,1H), 7.58 (d,1H), 7.34 (t,1H), 7.17(m,2H), 5.72 (br s,1H), 3.93 (s,3H), 2.72 (s,6H).

Step E: Preparation of5-chloro-2,4-dihydro-4-(7-methoxy-1-naphthalenyl)-2-methyl-3H-1,2,4-triazol-3-one

A solution of triphosgene (16.7 g) in ethyl acetate (130 mL) was heatedto reflux and a suspension of the title compound of Step D (4.9 g) inethyl acetate was added via cannula and the aid of a mechanical pumpover a period of 40 min. The temperature was held at approximately 75°C. during the addition. After the addition was complete, the reactionmixture was heated at reflux for 2 h, cooled to room temperature andstirred overnight at room temperature. The reaction mixture was pouredinto a solution of saturated aqueous sodium bicarbonate, extracted withethyl acetate, and the combined organic extracts were dried (MgSO₄),filtered and concentrated under reduced pressure to afford 4.9 g of thetitle compound of Step E as a white solid melting at 142-143° C. ¹ H NMR(CDCl₃): δ 7.93 (dd,1H), 7.84 (d,1H), 7.43 (m,2H), 7.24 (dd,1H), 6.75(d,1H), 3.87 (s,3H), 3.62 (s,3H).

Step F: Preparation of5-chloro-2,4-dihydro-4-(7-hydroxy-1-naphthalenyl)-2-methyl-3H-1,2,4-triazol-3-one

A solution of the title compound of Step E (2.9 g) in methylene chloride(35 mL) was cooled to 0° C. while stirring under N₂, and aluminumtrichloride (4.0 g) was added in portions. The reaction mixture wasallowed to warm to room temperature and then was heated to reflux for 18h. The reaction mixture was cooled to room temperature, poured intowater and extracted with ethyl acetate. The combined organic extractswere dried (MgSO₄), filtered and concentrated under reduced pressure.The crude material was purified by flash chromatography (1:4 ethylacetate:hexane as eluent) to afford 2.2 g of the title compound of StepF. ¹ H NMR (Me₂ SO-d₆): δ 10.08 (s,1H), 8.02 (d,1H), 7.95 (d,1H), 7.59(dd,1H), 7.41 (t,1H), 7.18 (dd,1H), 6.71 (d,1H), 3.49 (s,3H).

Step G: Preparation of2,4-dihydro-4-(7-hydroxy-1-naphthalenyl)-5-methoxy-2-methyl-3H-1,2,4-triazol-3-one

To a solution of the tide compound of Step F (3.3 g) in THF (38 mL) wasadded a solution of sodium methoxide (6.5 mL, 30% in methanol) whilestiring under N₂. The mixture was heated at 50° C. for 6 h and cooled toroom temperature and left to stir overnight. The reaction was quenchedwith water and extracted three times with methylene chloride and thenthree times with ethyl acetate. The combined organic extracts were dried(MgSO₄), filtered and concentrated under reduced pressure. Trituration(ethyl acetate:hexane 1:1) of the crude product provided 1.61 g of thetitle compound of Step G as a light brown solid melting at greater than250° C. ¹ H NMR (Me₂ SO-d₆): δ 10.00 (s,1H), 7.93 (m,2H), 7.47 (dd,1H),7.36 (t,1H), 7.15 (dd,1H), 6.73 (d,1H), 3.86 (s,3H), 3.39 (s,3H).

Step H: Preparation of5-chloro-3-[4-(trifluoromethyl)phenyl]-1,2,4-thiadiazole

A mixture of 4-(trifluoromethyl)benzamidine hydrochloride dihydrate (5.0g), water (50 mL), methylene chloride (100 mL), benzyltriethylammoniumchloride (0.44 g), and perchloromethyl mercaptan (2.1 mL) was preparedat room temperature and then cooled to 0° C. A solution of sodiumhydroxide (3.07 g) in water (50 mL) was added via an addition funnelwhile maintaining the temperature below 10° C. The reaction was left tostir overnight at room temperature. The mixture was transferred to aseparatory funnel and the two layers were separated. The organic layerwas washed with saturated sodium bicarbonate, dried (MgSO₄), filteredand concentrated under reduced pressure. The crude material was purifiedby flash chromatography (hexane as eluent) to afford 3.7 g of the titlecompound of Step H as a white powder. ¹ H NMR (CDCl₃): δ 8.36 (d,2H),7.73 (d,2H).

Step I: Preparation of2,4-dihydro-5-methoxy-2-methyl-4-[7-[[3-[4-(trifluoromethyl)phenyl]-1,2,4-thiadiazol-5-yl]oxy]-1-naphthalenyl]-3H-1,2,4-triazol-3-one

A solution of the title compound of Step G (214 mg) and the titlecompound of Step H (251 mg) in DMF (5 mL) was cooled to 0° C. under N₂.To the resulting yellow solution was added sodium hydride (25 mg) andthe mixture was left to stir overnight at room temperature. The reactionwas then cooled to 0° C., quenched with water and extracted twice withethyl acetate. The combined organic extracts were dried (MgSO₄),filtered and concentrated under reduced pressure. The crude yellow solidwas purified by crystallization in methanol to afford 216 mg of thetitle compound of Step I, a compound of the invention as a white powdermelting at 216-217° C. ¹ H NMR (Me₂ SO-d₆): δ 8.30 (m,3H), 8.23 (dd,1H),7.98 (d,1H), 7.91-7.81 (m,3H), 7.73 (m,2H), 3.86 (s,3H), 3.33 (s,3H).

EXAMPLE 8

Step A: Preparation of 3-nitro-2-(3-phenoxyphenoxy)pyridine

3-Phenoxyphenol (3 g, 16.1 mmol) was added to a solution of potassiumt-butoxide (1.90 g of 90%, 16.6 mmol) in 50 mL of dry tetrahydrofuran atroom temperature after which the reaction was stirred at roomtemperature for 10 min. Then, 2-chloro-3-nitropyridine (2.56 g, 16.1mmol) was added. The reaction mixture was stirred at room temperaturefor 16 h. The reaction mixture was concentrated under reduced pressure.The residue was diluted with water, extracted twice with methylenechloride and dried over magnesium sulfate. The solvent was then removedto yield the title compound of Step A as an oil. ¹ H NMR (CDCl₃ ; 300MHz): δ 6.85 (m,1H), 6.90 (m,2H), 7.0-7.2 (m,4H), 7.3-7.4 (m,3H), 8.35(m,2H).

Step B: Preparation of 3-isocyanato-2-(3-phenoxyphenoxy)pyridine

A solution of the entire amount of the intermediate in Step A and 6 mLwater in 60 mL acetic acid was heated on a steam bath to 65° C. and atthis temperature iron powder (3.05 g, 54.6 mmol) was added portionwisenoting the exotherm after each addition. The reaction temperature waskept between 65-85° C. by the addition rate and by a water cooling bath.After stirring for an additional 10 min at 85° C., the reaction wascooled to room temperature, diluted with methylene chloride and filteredthrough Celite®. The filtrate was washed once with water, then once withsaturated sodium bicarbonate, and dried over magnesium sulfate. Thesolvent was then removed under reduced pressure to yield an oil. Thisintermediate oil was then dissolved in 60 mL of dry toluene and to thissolution was added diphosgene (3.29 g, 16.6 mmol). The mixture was thenrefluxed with a water scrubber in place for 4 h. The reaction was cooledto room temperature, concentrated under reduced pressure to give crudetitle compound of Step B as solids which were used entirely in the nextreaction (Step C).

Step C: Preparation of5-chloro-2,4-dihydro-2-methyl-4-[2-(3-phenoxyphenoxy)-3-pyridinyl]-3H-1,2,4-triazol-3-one

The solids from Step B were dissolved in 100 mL of dry tetrahydrofuran.1,1-Dimethylhydrazine (3 g, 50.0 mmol) was added and the reactionmixture was stirred at room temperature for 16 h. The reaction mixturewas concentrated under reduced pressure. The residue was diluted withwater and extracted twice with diethyl ether. The combined organiclayers were then washed once with saturated aqueous NaCl solution anddried over magnesium sulfate. The solvent was removed under reducedpressure to give an oil. This oil was then dissolved in 200 mL methylenechloride and cooled to 0° C. at which temperature triphosgene (4.08 g,13.7 mmol) was added. The reaction mixture was refluxed for 16 h, cooledto room temperature and washed once with water. The organic layer wasthen dried over magnesium sulfate and concentrated under reducedpressure to yield a crude oil which was purified by silica gelchromatography using 3:2/hexanes:ethyl acetate as the eluent to yield 2g of the title compound of Step C, a compound of the invention, as asolid. ¹ H NMR (CDCl₃ ; 300 MHz): δ 3.53 (s,3H), 6.8-6.9 (m,3H), 7.0-7.2(m,4H), 7.3-7.4 (m,3H), 7.71 (dd,1H, J=1.9, 7.7 Hz), 8.27 (dd,1H, J=1.8,4.9 Hz).

EXAMPLE 9

Preparation of2,4-dihydro-5-methoxy-2-methyl-4-[2-(3-phenoxyphenoxy)-3-pyridinyl]-3H-1,2,4-triazol-3-one

The title compound of Step C in Example 8 (2 g, 5.26 mmol) was dissolvedin 100 mL of methanol and to this solution was added sodium methoxide(1.90 g 30% solution in methanol, 10.5 mmol) at room temperature. Thereaction was subsequently refluxed for 6 h, cooled to room temperatureand concentrated under reduced pressure to semisolids. The semisolidswere diluted with water, extracted twice with methylene chloride anddried over magnesium sulfate. The solvent was removed under reducedpressure to yield an oil which was subsequently purified by silica gelchromatography using 1:2/hexanes:ethyl acetate as the eluent to yield0.90 g of the title compound of Step D, compound of the invention, as asolid melting at 113-114° C. ¹ H NMR (CDCl₃ ; 400 MHz): δ 3.44 (s,3H),3.91 (s,3H), 6.80 (m,1H), 6.85 (m,2H), 7.06 (dd,2H, J=1.1, 8.6 Hz), 7.12(dd,2H, J=4.9, 7.6 Hz), 7.3-7.4 (m,3H), 7.71 (dd,1H, J=1.8, 7.6 Hz),8.21 (dd,1H, J=1.9, 4.9 Hz).

EXAMPLE 10

2,4-dihydro-5-methoxy-2-methyl-4-[2-[[[3-[4-(trifluoromethyl)phenyl]-1,2,4-thiadiazol-5-yl]oxy]methyl]-3-thienyl]-3H-1,2,4-triazol-3-one

A solution of the title compound of Step E in Example 1 (250 mg) and thetitle compound of Step H in Example 7 (329 mg) in DMF (5 mL) was cooledto 0° C. under N₂. To the resulting yellow solution was added sodiumhydride (32 mg) and the mixture was left to stir overnight at roomtemperature. The reaction mixture was poured into water and extractedthree times with CH₂ Cl₂. The combined organic extracts were dried(MgSO₄), filtered and concentrated under reduced pressure. The resultingcrude yellow solid was purified by crystallization in hexane:ethylacetate (1:1) to afford 191 mg of the title compound of Example 10, acompound of the invention, as a white powder melting at 138-139° C. ¹ HNMR (CDCl₃): δ 8.29 (d,2H), 7.71 (d,2H), 7.44 (d,1H), 6.98 (d,1H), 5.75(s,2H), 3.91 (s,3H), 3.43 (s,3H).

By the procedures described herein together with methods known in theart, the following compounds of Tables 1 to 21 can be prepared. Thefollowing abbreviations are used in the Tables which follow: t=tertiary,s=secondary, n=normal, i=iso, c=cyclo, Me=methyl, Et=ethyl, Pr=propyl,i-Pr=isopropyl, Bu=butyl, Ph=phenyl, nap=naphthalenyl, MeO=methoxy,EtO=ethoxy, PhO=phenoxy, MeS=methylthio, EtS=ethylthio, CN=cyano, NO₂=nitro, TMS=trimethylsilyl, S(O)Me=methylsulfinyl, and S(O)₂Me=methylsulfonyl.

                                      TABLE 1                                     __________________________________________________________________________    Compounds of Formula I where A = N, G = N, W = O, X = OMe, R.sup.2 = Me,       Y = CH.sub.2 O--N═C(Me), Z = 3-CF.sub.3 -Ph, the floating double         bond is attached to A and                                                     E--Y--Z   E--Y--Z      E--Y--Z      E--Y--Z       E--Y--Z                     __________________________________________________________________________                                                        #STR40##                                                                      #STR41##                                                                      #STR42##                                                                      #STR43##                                                                      #STR44##                     -                                                                                                                              #STR45##                                                                      #STR46##                                                                      #STR47##                                                                      #STR48##                                                                      #STR49##                     -                                                                                                                              #STR50##                                                                      #STR51##                                                                      #STR52##                                                                      #STR53##                                                                      #STR54##                     -                                                                                                                              #STR55##                                                                      #STR56##                                                                      #STR57##                                                                      #STR58##                                                                      #STR59##                     -                                                                                                                              #STR60##                                                                      #STR61##                                                                      #STR62##                                                                      #STR63##                                                                      #STR64##                  __________________________________________________________________________

                                      TABLE 2                                     __________________________________________________________________________    Compounds of Formula I where A = O, G = C, W = O, X = OMe, R.sup.2 = Me,       Y = CH.sub.2 O--N═C(Me), Z = 3-CF.sub.3 -Ph, the floating double         bond is attached to G and                                                     E--Y--Z   E--Y--Z      E--Y--Z      E--Y--Z       E--Y--Z                     __________________________________________________________________________                                                        #STR65##                                                                      #STR66##                                                                      #STR67##                                                                      #STR68##                                                                      #STR69##                     -                                                                                                                              #STR70##                                                                      #STR71##                                                                      #STR72##                                                                      #STR73##                                                                      #STR74##                     -                                                                                                                              #STR75##                                                                      #STR76##                                                                      #STR77##                                                                      #STR78##                                                                      #STR79##                     -                                                                                                                              #STR80##                                                                      #STR81##                                                                      #STR82##                                                                      #STR83##                                                                      #STR84##                     -                                                                                                                              #STR85##                                                                      #STR86##                                                                      #STR87##                                                                      #STR88##                                                                      #STR89##                  __________________________________________________________________________

                  TABLE 3                                                         ______________________________________                                        Compounds of Formula I defined as:                                               -                                                                            #STR90##                                                                       -                                                                              Y                  Y                                                      ______________________________________                                        Z = 3-CF.sub.3 -Ph                                                                S                  CH.sub.2 CH.sub.2                                        CH═CH CH(Me)CH.sub.2                                                      C(Me)═CH CH.sub.2 CH(Me)                                                  CH═C(Me) CH(Me)CH(Me)                                                     C(Me)═C(Me) CH.sub.2 O                                                    S(O).sub.2 CH═C(Cl)C(═O)O                                             CH.sub.2 O--N═C(CN) CH═N--O--CH.sub.2                                 CH.sub.2 O--N═C(c-Pr) CH═N--O--CH(Me)                                 CH.sub.2 O--N═C(CN)C(═O) CH.sub.2 O--N═C(Et)                      CH.sub.2 O--N═C(NHMe) CH.sub.2 O--N═C(NH.sub.2)                       CH.sub.2 O--N(Me)C(═O)N(Me) CH.sub.2 O--N(Me)C(═S)N(Me)                                     CH.sub.2 SC(SMe)═N CH═N--N(Me)                  CH.sub.2 OC(═O)O CH.sub.2 OC(═S)O                                     CH.sub.2 SC(═O)N(Me) CH.sub.2 SC(═O)NH                                CH.sub.2 SC(═O)O CH.sub.2 SC(═S)O                                     CH.sub.2 SC(═NMe)S CH.sub.2 N(Me)C(═O)N(Me)                           CH.sub.2 O--N═C(Me)CH.sub.2 S CH.sub.2 O--N═C(SMe)CH.sub.2 S                                O--N═CH O--N═C(Me)                              S(O) CH.sub.2 SC(Et)═N                                                    CH(Me)O SCH.sub.2                                                             OCH.sub.2 SCH(Me)                                                             OCH(Me) CH.sub.2 O--N═CH                                                  CH.sub.2 S                                                                    CH(Me)S CH═N--O                                                           O C(═O)                                                                   CH.sub.2 OC(═O)NH CH.sub.2 O--N═C(SMe)                                CH.sub.2 O--N═C(OMe) N═C(Cl)C(═O)O                                CH.sub.2 O--N═C(Cl) CH.sub.2 O--N═C(CF.sub.3)                         CH.sub.2 CO(═S)NH CH.sub.2 OC(═S)N(Me)                                CH.sub.2 O--N═C(Me)N(Me) CH.sub.2 O--N═C(Me)OCH.sub.2                 CH.sub.2 O--N═C(Me)N═N CH.sub.2 N(Me)--N═C(Me)                    CH.sub.2 OC(═O)S CH.sub.2 OC(═S)S                                     CH.sub.2 SC(═S)N(Me) CH.sub.2 SC(═S)S                                 CH.sub.2 SC(═O)S CH.sub.2 O--N═C(SMe)CH.sub.2 O                       CH.sub.2 O--N═C(Me)CH.sub.2 O CH.sub.2 OC(Me)═C(CN)                   OCH.sub.2 CH.sub.2 O--N═C(Me) C(Me)═N--O                              CH═N--N═C(Me) C.tbd.C                                                 C.tbd.C--C(═O)O CH.sub.2 SC(c-Pr)═N                                 Z = 3-Me.sub.3 Si--Ph                                                             S                  CH.sub.2 CH.sub.2                                        CH═CH CH(Me)CH.sub.2                                                      C(Me)═CH CH.sub.2 CH(Me)                                                  CH═C(Me) CH(Me)CH(Me)                                                     C(Me)═C(Me) CH.sub.2 O                                                    S(O).sub.2 CH═C(Cl)C(═O)O                                             CH.sub.2 O--N═C(CN) CH═N--O--CH.sub.2                                 CH.sub.2 O--N═C(c-Pr) CH═N--O--CH(Me)                                 CH.sub.2 O--N═C(CN)C(═O) CH.sub.2 O--N═C(Et)                      CH.sub.2 O--N═C(NHMe) CH.sub.2 O--N═C(NH.sub.2)                       CH.sub.2 O--N(Me)C(═O)N(Me) CH.sub.2 O--N(Me)C(═S)N(Me)                                     CH.sub.2 SC(SMe)═N CH═N--N(Me)                  CH.sub.2 OC(═O)O CH.sub.2 OC(═S)O                                     CH.sub.2 SC(═O)N(Me) CH.sub.2 SC(═O)NH                                CH.sub.2 SC(═O)O CH.sub.2 SC(═S)O                                     CH.sub.2 SC(═NMe)S CH.sub.2 N(Me)C(═O)N(Me)                           CH.sub.2 O--N═C(Me)CH.sub.2 S CH.sub.2 O--N═C(SMe)CH.sub.2 S                                O--N═CH O--N═C(Me)                              S(O) CH.sub.2 SC(Et)═N                                                    CH(Me)O SCH.sub.2                                                             OCH.sub.2 SCH(Me)                                                             OCH(Me) CH.sub.2 O--N═CH                                                  CH.sub.2 S                                                                    CH(Me)S CH═N--O                                                           O C(═O)                                                                   CH.sub.2 OC(═O)NH CH.sub.2 O--N═C(SMe)                                CH.sub.2 O--N═C(OMe) N═C(Cl)C(═O)O                                CH.sub.2 O--N═C(Cl) CH.sub.2 O--N═C(CF.sub.3)                         CH.sub.2 CO(═S)NH CH.sub.2 OC(═S)N(Me)                                CH.sub.2 O--N═C(Me)N(Me) CH.sub.2 O--N═C(Me)OCH.sub.2                 CH.sub.2 O--N═C(Me)N═N CH.sub.2 N(Me)--N═C(Me)                    CH.sub.2 OC(═O)S CH.sub.2 OC(═S)S                                     CH.sub.2 SC(═S)N(Me) CH.sub.2 SC(═S)S                                 CH.sub.2 SC(═O)S CH.sub.2 O--N═C(SMe)CH.sub.2 O                       CH.sub.2 O--N═C(Me)CH.sub.2 O CH.sub.2 OC(Me)═C(CN)                   OCH.sub.2 CH.sub.2 O--N═C(Me) C(Me)═N--O                              CH═N--N═C(Me) C.tbd.C                                                 C.tbd.C--C(═O)O CH.sub.2 SC(c-Pr)═N                                 Z = 4-CF.sub.3 -2-pyridinyl                                                       S                  CH.sub.2 CH.sub.2                                        CH═CH CH(Me)CH.sub.2                                                      C(Me)═CH CH.sub.2 CH(Me)                                                  CH═C(Me) CH(Me)CH(Me)                                                     C(Me)═C(Me) CH.sub.2 O                                                    S(O).sub.2 CH═C(Cl)C(═O)O                                             CH.sub.2 O--N═C(CN) CH═N--O--CH.sub.2                                 CH.sub.2 O--N═C(c-Pr) CH═N--O--CH(Me)                                 CH.sub.2 O--N═C(CN)C(═O) CH.sub.2 O--N═C(Et)                      CH.sub.2 O--N═C(NHMe) CH.sub.2 O--N═C(NH.sub.2)                       CH.sub.2 O--N(Me)C(═O)N(Me) CH.sub.2 O--N(Me)C(═S)N(Me)                                     CH.sub.2 SC(SMe)═N CH═N--N(Me)                  CH.sub.2 OC(═O)O CH.sub.2 OC(═S)O                                     CH.sub.2 SC(═O)N(Me) CH.sub.2 SC(═O)NH                                CH.sub.2 SC(═O)O CH.sub.2 SC(═S)O                                     CH.sub.2 SC(═NMe)S CH.sub.2 N(Me)C(═O)N(Me)                           CH.sub.2 O--N═C(Me)CH.sub.2 S CH.sub.2 O--N═C(SMe)CH.sub.2 S                                O--N═CH O--N═C(Me)                              S(O) CH.sub.2 SC(Et)═N                                                    CH(Me)O SCH.sub.2                                                             OCH.sub.2 SCH(Me)                                                             OCH(Me) CH.sub.2 O--N═CH                                                  CH.sub.2 S                                                                    CH(Me)S CH═N--O                                                           O C(═O)                                                                   CH.sub.2 OC(═O)NH CH.sub.2 O--N═C(SMe)                                CH.sub.2 O--N═C(OMe) N═C(Cl)C(═O)O                                CH.sub.2 O--N═C(Cl) CH.sub.2 O--N═C(CF.sub.3)                         CH.sub.2 OC(═S)NH CH.sub.2 OC(═S)N(Me)                                CH.sub.2 O--N═C(Me)N(Me) CH.sub.2 O--N═C(Me)OCH.sub.2                 CH.sub.2 O--N═C(Me)N═N CH.sub.2 N(Me)--N═C(Me)                    CH.sub.2 OC(═O)S CH.sub.2 OC(═S)S                                     CH.sub.2 SC(═S)N(Me) CH.sub.2 SC(═S)S                                 CH.sub.2 SC(═O)S CH.sub.2 O--N═C(SMe)CH.sub.2 O                       CH.sub.2 O--N═C(Me)CH.sub.2 O CH.sub.2 OC(Me)═C(CN)                   OCH.sub.2 CH.sub.2 O--N═C(Me) C(Me)═N--O                              CH═N--N═C(Me) C.tbd.C                                                 C.tbd.C--C(═O)O CH.sub.2 SC(c-Pr)═N                                 ______________________________________                                    

                  TABLE 4                                                         ______________________________________                                        Compounds of Formula I defined as:                                               -                                                                            #STR91##                                                                       -                                                                              Y                  Y                                                      ______________________________________                                        Z = 3-CF.sub.3 -Ph                                                                S                  CH.sub.2 CH.sub.2                                        CH═CH CH(Me)CH.sub.2                                                      C(Me)═CH CH.sub.2 CH(Me)                                                  CH═C(Me) CH(Me)CH(Me)                                                     C(Me)═C(Me) CH.sub.2 O                                                    S(O).sub.2 CH═C(Cl)C(═O)O                                             CH.sub.2 O--N═C(CN) CH═N--O--CH.sub.2                                 CH.sub.2 O--N═C(c-Pr) CH═N--O--CH(Me)                                 CH.sub.2 O--N═C(CN)C(═O) CH.sub.2 O--N═C(Et)                      CH.sub.2 O--N═C(NHMe) CH.sub.2 O--N═C(NH.sub.2)                       CH.sub.2 O--N(Me)C(═O)N(Me) CH.sub.2 O--N(Me)C(═S)N(Me)                                     CH.sub.2 SC(SMe)═N CH═N--N(Me)                  CH.sub.2 OC(═O)O CH.sub.2 OC(═S)O                                     CH.sub.2 SC(═O)N(Me) CH.sub.2 SC(═O)NH                                CH.sub.2 SC(═O)O CH.sub.2 SC(═S)O                                     CH.sub.2 SC(═NMe)S CH.sub.2 N(Me)C(═O)N(Me)                           CH.sub.2 O--N═C(Me)CH.sub.2 S CH.sub.2 O--N═C(SMe)CH.sub.2 S                                O--N═CH O--N═C(Me)                              S(O) CH.sub.2 SC(Et)═N                                                    CH(Me)O SCH.sub.2                                                             OCH.sub.2 SCH(Me)                                                             OCH(Me) CH.sub.2 O--N═CH                                                  CH.sub.2 S                                                                    CH(Me)S CH═N--O                                                           O C(═O)                                                                   CH.sub.2 OC(═O)NH CH.sub.2 O--N═C(SMe)                                CH.sub.2 O--N═C(OMe) N═C(Cl)C(═O)O                                CH.sub.2 O--N═C(Cl) CH.sub.2 O--N═C(CF.sub.3)                         CH.sub.2 CO(═S)NH CH.sub.2 OC(═S)N(Me)                                CH.sub.2 O--N═C(Me)N(Me) CH.sub.2 O--N═C(Me)OCH.sub.2                 CH.sub.2 O--N═C(Me)N═N CH.sub.2 N(Me)--N═C(Me)                    CH.sub.2 OC(═O)S CH.sub.2 OC(═S)S                                     CH.sub.2 SC(═S)N(Me) CH.sub.2 SC(═S)S                                 CH.sub.2 SC(═O)S CH.sub.2 O--N═C(SMe)CH.sub.2 O                       CH.sub.2 O--N═C(Me)CH.sub.2 O CH.sub.2 OC(Me)═C(CN)                   OCH.sub.2 CH.sub.2 O--N═C(Me) C(Me)═N--O                              CH═N--N═C(Me) C.tbd.C                                                 C.tbd.C--C(═O)O CH.sub.2 SC(c-Pr)═N                                 Z = 3-Me.sub.3 Si--Ph                                                             S                  CH.sub.2 CH.sub.2                                        CH═CH CH(Me)CH.sub.2                                                      C(Me)═CH CH.sub.2 CH(Me)                                                  CH═C(Me) CH(Me)CH(Me)                                                     C(Me)═C(Me) CH.sub.2 O                                                    S(O).sub.2 CH═C(Cl)C(═O)O                                             CH.sub.2 O--N═C(CN) CH═N--O--CH.sub.2                                 CH.sub.2 O--N═C(c-Pr) CH═N--O--CH(Me)                                 CH.sub.2 O--N═C(CN)C(═O) CH.sub.2 O--N═C(Et)                      CH.sub.2 O--N═C(NHMe) CH.sub.2 O--N═C(NH.sub.2)                       CH.sub.2 O--N(Me)C(═O)N(Me) CH.sub.2 O--N(Me)C(═S)N(Me)                                     CH.sub.2 SC(SMe)═N CH═N--N(Me)                  CH.sub.2 OC(═O)O CH.sub.2 OC(═S)O                                     CH.sub.2 SC(═O)N(Me) CH.sub.2 SC(═O)NH                                CH.sub.2 SC(═O)O CH.sub.2 SC(═S)O                                     CH.sub.2 SC(═NMe)S CH.sub.2 N(Me)C(═O)N(Me)                           CH.sub.2 O--N═C(Me)CH.sub.2 S CH.sub.2 O--N═C(SMe)CH.sub.2 S                                O--N═CH O--N═C(Me)                              S(O) CH.sub.2 SC(Et)═N                                                    CH(Me)O SCH.sub.2                                                             OCH.sub.2 SCH(Me)                                                             OCH(Me) CH.sub.2 O--N═CH                                                  CH.sub.2 S                                                                    CH(Me)S CH═N--O                                                           O C(═O)                                                                   CH.sub.2 OC(═O)NH CH.sub.2 O--N═C(SMe)                                CH.sub.2 O--N═C(OMe) N═C(Cl)C(═O)O                                CH.sub.2 O--N═C(Cl) CH.sub.2 O--N═C(CF.sub.3)                         CH.sub.2 CO(═S)NH CH.sub.2 OC(═S)N(Me)                                CH.sub.2 O--N═C(Me)N(Me) CH.sub.2 O--N═C(Me)OCH.sub.2                 CH.sub.2 O--N═C(Me)N═N CH.sub.2 N(Me)--N═C(Me)                    CH.sub.2 OC(═O)S CH.sub.2 OC(═S)S                                     CH.sub.2 SC(═S)N(Me) CH.sub.2 SC(═S)S                                 CH.sub.2 SC(═O)S CH.sub.2 O--N═C(SMe)CH.sub.2 O                       CH.sub.2 O--N═C(Me)CH.sub.2 O CH.sub.2 OC(Me)═C(CN)                   OCH.sub.2 CH.sub.2 O--N═C(Me) C(Me)═N--O                              CH═N--N═C(Me) C.tbd.C                                                 C.tbd.C--C(═O)O CH.sub.2 SC(c-Pr)═N                                 Z = 4-CF.sub.3 -2-pyridinyl                                                       S                  CH.sub.2 CH.sub.2                                        CH═CH CH(Me)CH.sub.2                                                      C(Me)═CH CH.sub.2 CH(Me)                                                  CH═C(Me) CH(Me)CH(Me)                                                     C(Me)═C(Me) CH.sub.2 O                                                    S(O).sub.2 CH═C(Cl)C(═O)O                                             CH.sub.2 O--N═C(CN) CH═N--O--CH.sub.2                                 CH.sub.2 O--N═C(c-Pr) CH═N--O--CH(Me)                                 CH.sub.2 O--N═C(CN)C(═O) CH.sub.2 O--N═C(Et)                      CH.sub.2 O--N═C(NHMe) CH.sub.2 O--N═C(NH.sub.2)                       CH.sub.2 O--N(Me)C(═O)N(Me) CH.sub.2 O--N(Me)C(═S)N(Me)                                     CH.sub.2 SC(SMe)═N CH═N--N(Me)                  CH.sub.2 OC(═O)O CH.sub.2 OC(═S)O                                     CH.sub.2 SC(═O)N(Me) CH.sub.2 SC(═O)NH                                CH.sub.2 SC(═O)O CH.sub.2 SC(═S)O                                     CH.sub.2 SC(═NMe)S CH.sub.2 N(Me)C(═O)N(Me)                           CH.sub.2 O--N═C(Me)CH.sub.2 S CH.sub.2 O--N═C(SMe)CH.sub.2 S                                O--N═CH O--N═C(Me)                              S(O) CH.sub.2 SC(Et)═N                                                    CH(Me)O SCH.sub.2                                                             OCH.sub.2 SCH(Me)                                                             OCH(Me) CH.sub.2 O--N═CH                                                  CH.sub.2 S                                                                    CH(Me)S CH═N--O                                                           O C(═O)                                                                   CH.sub.2 OC(═O)NH CH.sub.2 O--N═C(SMe)                                CH.sub.2 O--N═C(OMe) N═C(Cl)C(═O)O                                CH.sub.2 O--N═C(Cl) CH.sub.2 O--N═C(CF.sub.3)                         CH.sub.2 OC(═S)NH CH.sub.2 OC(═S)N(Me)                                CH.sub.2 O--N═C(Me)N(Me) CH.sub.2 O--N═C(Me)OCH.sub.2                 CH.sub.2 O--N═C(Me)N═N CH.sub.2 N(Me)--N═C(Me)                    CH.sub.2 OC(═O)S CH.sub.2 OC(═S)S                                     CH.sub.2 SC(═S)N(Me) CH.sub.2 SC(═S)S                                 CH.sub.2 SC(═O)S CH.sub.2 O--N═C(SMe)CH.sub.2 O                       CH.sub.2 O--N═C(Me)CH.sub.2 O CH.sub.2 OC(Me)═C(CN)                   OCH.sub.2 CH.sub.2 O--N═C(Me) C(Me)═N--O                              CH═N--N═C(Me) C.tbd.C                                                 C.tbd.C--C(═O)O CH.sub.2 SC(c-Pr)═N                                 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                  TABLE 5                                                         ______________________________________                                        Compounds of Formula I defined as:                                               -                                                                            #STR92##                                                                       -                                                                              Y                  Y                                                      ______________________________________                                        Z = 3-CF.sub.3 -Ph                                                                S                  CH.sub.2 CH.sub.2                                        CH═CH CH(Me)CH.sub.2                                                      C(Me)═CH CH.sub.2 CH(Me)                                                  CH═C(Me) CH(Me)CH(Me)                                                     C(Me)═C(Me) CH.sub.2 O                                                    S(O).sub.2 CH═C(Cl)C(═O)O                                             CH.sub.2 O--N═C(CN) CH═N--O--CH.sub.2                                 CH.sub.2 O--N═C(c-Pr) CH═N--O--CH(Me)                                 CH.sub.2 O--N═C(CN)C(═O) CH.sub.2 O--N═C(Et)                      CH.sub.2 O--N═C(NHMe) CH.sub.2 O--N═C(NH.sub.2)                       CH.sub.2 O--N(Me)C(═O)N(Me) CH.sub.2 O--N(Me)C(═S)N(Me)                                     CH.sub.2 SC(SMe)═N CH═N--N(Me)                  CH.sub.2 OC(═O)O CH.sub.2 OC(═S)O                                     CH.sub.2 SC(═O)N(Me) CH.sub.2 SC(═O)NH                                CH.sub.2 SC(═O)O CH.sub.2 SC(═S)O                                     CH.sub.2 SC(═NMe)S CH.sub.2 N(Me)C(═O)N(Me)                           CH.sub.2 O--N═C(Me)CH.sub.2 S CH.sub.2 O--N═C(SMe)CH.sub.2 S                                O--N═CH O--N═C(Me)                              S(O) CH.sub.2 SC(Et)═N                                                    CH(Me)O SCH.sub.2                                                             OCH.sub.2 SCH(Me)                                                             OCH(Me) CH.sub.2 O--N═CH                                                  CH.sub.2 S                                                                    CH(Me)S CH═N--O                                                           O C(═O)                                                                   CH.sub.2 OC(═O)NH CH.sub.2 O--N═C(SMe)                                CH.sub.2 O--N═C(OMe) N═C(Cl)C(═O)O                                CH.sub.2 O--N═C(Cl) CH.sub.2 O--N═C(CF.sub.3)                         CH.sub.2 CO(═S)NH CH.sub.2 OC(═S)N(Me)                                CH.sub.2 O--N═C(Me)N(Me) CH.sub.2 O--N═C(Me)OCH.sub.2                 CH.sub.2 O--N═C(Me)N═N CH.sub.2 N(Me)--N═C(Me)                    CH.sub.2 OC(═O)S CH.sub.2 OC(═S)S                                     CH.sub.2 SC(═S)N(Me) CH.sub.2 SC(═S)S                                 CH.sub.2 SC(═O)S CH.sub.2 O--N═C(SMe)CH.sub.2 O                       CH.sub.2 O--N═C(Me)CH.sub.2 O CH.sub.2 OC(Me)═C(CN)                   OCH.sub.2 CH.sub.2 O--N═C(Me) C(Me)═N--O                              CH═N--N═C(Me) C.tbd.C                                                 C.tbd.C--C(═O)O CH.sub.2 SC(c-Pr)═N                                 Z = 3-Me.sub.3 Si--Ph                                                             S                  CH.sub.2 CH.sub.2                                        CH═CH CH(Me)CH.sub.2                                                      C(Me)═CH CH.sub.2 CH(Me)                                                  CH═C(Me) CH(Me)CH(Me)                                                     C(Me)═C(Me) CH.sub.2 O                                                    S(O).sub.2 CH═C(Cl)C(═O)O                                             CH.sub.2 O--N═C(CN) CH═N--O--CH.sub.2                                 CH.sub.2 O--N═C(c-Pr) CH═N--O--CH(Me)                                 CH.sub.2 O--N═C(CN)C(═O) CH.sub.2 O--N═C(Et)                      CH.sub.2 O--N═C(NHMe) CH.sub.2 O--N═C(NH.sub.2)                       CH.sub.2 O--N(Me)C(═O)N(Me) CH.sub.2 O--N(Me)C(═S)N(Me)                                     CH.sub.2 SC(SMe)═N CH═N--N(Me)                  CH.sub.2 OC(═O)O CH.sub.2 OC(═S)O                                     CH.sub.2 SC(═O)N(Me) CH.sub.2 SC(═O)NH                                CH.sub.2 SC(═O)O CH.sub.2 SC(═S)O                                     CH.sub.2 SC(═NMe)S CH.sub.2 N(Me)C(═O)N(Me)                           CH.sub.2 O--N═C(Me)CH.sub.2 S CH.sub.2 O--N═C(SMe)CH.sub.2 S                                O--N═CH O--N═C(Me)                              S(O) CH.sub.2 SC(Et)═N                                                    CH(Me)O SCH.sub.2                                                             OCH.sub.2 SCH(Me)                                                             OCH(Me) CH.sub.2 O--N═CH                                                  CH.sub.2 S                                                                    CH(Me)S CH═N--O                                                           O C(═O)                                                                   CH.sub.2 OC(═O)NH CH.sub.2 O--N═C(SMe)                                CH.sub.2 O--N═C(OMe) N═C(Cl)C(═O)O                                CH.sub.2 O--N═C(Cl) CH.sub.2 O--N═C(CF.sub.3)                         CH.sub.2 CO(═S)NH CH.sub.2 OC(═S)N(Me)                                CH.sub.2 O--N═C(Me)N(Me) CH.sub.2 O--N═C(Me)OCH.sub.2                 CH.sub.2 O--N═C(Me)N═N CH.sub.2 N(Me)--N═C(Me)                    CH.sub.2 OC(═O)S CH.sub.2 OC(═S)S                                     CH.sub.2 SC(═S)N(Me) CH.sub.2 SC(═S)S                                 CH.sub.2 SC(═O)S CH.sub.2 O--N═C(SMe)CH.sub.2 O                       CH.sub.2 O--N═C(Me)CH.sub.2 O CH.sub.2 OC(Me)═C(CN)                   OCH.sub.2 CH.sub.2 O--N═C(Me) C(Me)═N--O                              CH═N--N═C(Me) C.tbd.C                                                 C.tbd.C--C(═O)O CH.sub.2 SC(c-Pr)═N                                 Z = 4-CF.sub.3 -2-pyridinyl                                                       S                  CH.sub.2 CH.sub.2                                        CH═CH CH(Me)CH.sub.2                                                      C(Me)═CH CH.sub.2 CH(Me)                                                  CH═C(Me) CH(Me)CH(Me)                                                     C(Me)═C(Me) CH.sub.2 O                                                    S(O).sub.2 CH═C(Cl)C(═O)O                                             CH.sub.2 O--N═C(CN) CH═N--O--CH.sub.2                                 CH.sub.2 O--N═C(c-Pr) CH═N--O--CH(Me)                                 CH.sub.2 O--N═C(CN)C(═O) CH.sub.2 O--N═C(Et)                      CH.sub.2 O--N═C(NHMe) CH.sub.2 O--N═C(NH.sub.2)                       CH.sub.2 O--N(Me)C(═O)N(Me) CH.sub.2 O--N(Me)C(═S)N(Me)                                     CH.sub.2 SC(SMe)═N CH═N--N(Me)                  CH.sub.2 OC(═O)O CH.sub.2 OC(═S)O                                     CH.sub.2 SC(═O)N(Me) CH.sub.2 SC(═O)NH                                CH.sub.2 SC(═O)O CH.sub.2 SC(═S)O                                     CH.sub.2 SC(═NMe)S CH.sub.2 N(Me)C(═O)N(Me)                           CH.sub.2 O--N═C(Me)CH.sub.2 S CH.sub.2 O--N═C(SMe)CH.sub.2 S                                O--N═CH O--N═C(Me)                              S(O) CH.sub.2 SC(Et)═N                                                    CH(Me)O SCH.sub.2                                                             OCH.sub.2 SCH(Me)                                                             OCH(Me) CH.sub.2 O--N═CH                                                  CH.sub.2 S                                                                    CH(Me)S CH═N--O                                                           O C(═O)                                                                   CH.sub.2 OC(═O)NH CH.sub.2 O--N═C(SMe)                                CH.sub.2 O--N═C(OMe) N═C(Cl)C(═O)O                                CH.sub.2 O--N═C(Cl) CH.sub.2 O--N═C(CF.sub.3)                         CH.sub.2 OC(═S)NH CH.sub.2 OC(═S)N(Me)                                CH.sub.2 O--N═C(Me)N(Me) CH.sub.2 O--N═C(Me)OCH.sub.2                 CH.sub.2 O--N═C(Me)N═N CH.sub.2 N(Me)--N═C(Me)                    CH.sub.2 OC(═O)S CH.sub.2 OC(═S)S                                     CH.sub.2 SC(═S)N(Me) CH.sub.2 SC(═S)S                                 CH.sub.2 SC(═O)S CH.sub.2 O--N═C(SMe)CH.sub.2 O                       CH.sub.2 O--N═C(Me)CH.sub.2 O CH.sub.2 OC(Me)═C(CN)                   OCH.sub.2 CH.sub.2 O--N═C(Me) C(Me)═N--O                              CH═N--N═C(Me) C.tbd.C                                                 C.tbd.C--C(═O)O CH.sub.2 SC(c-Pr)═N                                 ______________________________________                                    

                  TABLE 6                                                         ______________________________________                                        Compounds of Formula I defined as:                                               -                                                                            #STR93##                                                                       -                                                                              Y                  Y                                                      ______________________________________                                        Z = 3-CF.sub.3 -Ph                                                                S                  CH.sub.2 CH.sub.2                                        CH═CH CH(Me)CH.sub.2                                                      C(Me)═CH CH.sub.2 CH(Me)                                                  CH═C(Me) CH(Me)CH(Me)                                                     C(Me)═C(Me) CH.sub.2 O                                                    S(O).sub.2 CH═C(Cl)C(═O)O                                             CH.sub.2 O--N═C(CN) CH═N--O--CH.sub.2                                 CH.sub.2 O--N═C(c-Pr) CH═N--O--CH(Me)                                 CH.sub.2 O--N═C(CN)C(═O) CH.sub.2 O--N═C(Et)                      CH.sub.2 O--N═C(NHMe) CH.sub.2 O--N═C(NH.sub.2)                       CH.sub.2 O--N(Me)C(═O)N(Me) CH.sub.2 O--N(Me)C(═S)N(Me)                                     CH.sub.2 SC(SMe)═N CH═N--N(Me)                  CH.sub.2 OC(═O)O CH.sub.2 OC(═S)O                                     CH.sub.2 SC(═O)N(Me) CH.sub.2 SC(═O)NH                                CH.sub.2 SC(═O)O CH.sub.2 SC(═S)O                                     CH.sub.2 SC(═NMe)S CH.sub.2 N(Me)C(═O)N(Me)                           CH.sub.2 O--N═C(Me)CH.sub.2 S CH.sub.2 O--N═C(SMe)CH.sub.2 S                                O--N═CH O--N═C(Me)                              S(O) CH.sub.2 SC(Et)═N                                                    CH(Me)O SCH.sub.2                                                             OCH.sub.2 SCH(Me)                                                             OCH(Me) CH.sub.2 O--N═CH                                                  CH.sub.2 S                                                                    CH(Me)S CH═N--O                                                           O C(═O)                                                                   CH.sub.2 OC(═O)NH CH.sub.2 O--N═C(SMe)                                CH.sub.2 O--N═C(OMe) N═C(Cl)C(═O)O                                CH.sub.2 O--N═C(Cl) CH.sub.2 O--N═C(CF.sub.3)                         CH.sub.2 CO(═S)NH CH.sub.2 OC(═S)N(Me)                                CH.sub.2 O--N═C(Me)N(Me) CH.sub.2 O--N═C(Me)OCH.sub.2                 CH.sub.2 O--N═C(Me)N═N CH.sub.2 N(Me)--N═C(Me)                    CH.sub.2 OC(═O)S CH.sub.2 OC(═S)S                                     CH.sub.2 SC(═S)N(Me) CH.sub.2 SC(═S)S                                 CH.sub.2 SC(═O)S CH.sub.2 O--N═C(SMe)CH.sub.2 O                       CH.sub.2 O--N═C(Me)CH.sub.2 O CH.sub.2 OC(Me)═C(CN)                   OCH.sub.2 CH.sub.2 O--N═C(Me) C(Me)═N--O                              CH═N--N═C(Me) C.tbd.C                                                 C.tbd.C--C(═O)O CH.sub.2 SC(c-Pr)═N                                 Z = 3-Me.sub.3 Si--Ph                                                             S                  CH.sub.2 CH.sub.2                                        CH═CH CH(Me)CH.sub.2                                                      C(Me)═CH CH.sub.2 CH(Me)                                                  CH═C(Me) CH(Me)CH(Me)                                                     C(Me)═C(Me) CH.sub.2 O                                                    S(O).sub.2 CH═C(Cl)C(═O)O                                             CH.sub.2 O--N═C(CN) CH═N--O--CH.sub.2                                 CH.sub.2 O--N═C(c-Pr) CH═N--O--CH(Me)                                 CH.sub.2 O--N═C(CN)C(═O) CH.sub.2 O--N═C(Et)                      CH.sub.2 O--N═C(NHMe) CH.sub.2 O--N═C(NH.sub.2)                       CH.sub.2 O--N(Me)C(═O)N(Me) CH.sub.2 O--N(Me)C(═S)N(Me)                                     CH.sub.2 SC(SMe)═N CH═N--N(Me)                  CH.sub.2 OC(═O)O CH.sub.2 OC(═S)O                                     CH.sub.2 SC(═O)N(Me) CH.sub.2 SC(═O)NH                                CH.sub.2 SC(═O)O CH.sub.2 SC(═S)O                                     CH.sub.2 SC(═NMe)S CH.sub.2 N(Me)C(═O)N(Me)                           CH.sub.2 O--N═C(Me)CH.sub.2 S CH.sub.2 O--N═C(SMe)CH.sub.2 S                                O--N═CH O--N═C(Me)                              S(O) CH.sub.2 SC(Et)═N                                                    CH(Me)O SCH.sub.2                                                             OCH.sub.2 SCH(Me)                                                             OCH(Me) CH.sub.2 O--N═CH                                                  CH.sub.2 S                                                                    CH(Me)S CH═N--O                                                           O C(═O)                                                                   CH.sub.2 OC(═O)NH CH.sub.2 O--N═C(SMe)                                CH.sub.2 O--N═C(OMe) N═C(Cl)C(═O)O                                CH.sub.2 O--N═C(Cl) CH.sub.2 O--N═C(CF.sub.3)                         CH.sub.2 CO(═S)NH CH.sub.2 OC(═S)N(Me)                                CH.sub.2 O--N═C(Me)N(Me) CH.sub.2 O--N═C(Me)OCH.sub.2                 CH.sub.2 O--N═C(Me)N═N CH.sub.2 N(Me)--N═C(Me)                    CH.sub.2 OC(═O)S CH.sub.2 OC(═S)S                                     CH.sub.2 SC(═S)N(Me) CH.sub.2 SC(═S)S                                 CH.sub.2 SC(═O)S CH.sub.2 O--N═C(SMe)CH.sub.2 O                       CH.sub.2 O--N═C(Me)CH.sub.2 O CH.sub.2 OC(Me)═C(CN)                   OCH.sub.2 CH.sub.2 O--N═C(Me) C(Me)═N--O                              CH═N--N═C(Me) C.tbd.C                                                 C.tbd.C--C(═O)O CH.sub.2 SC(c-Pr)═N                                 Z = 4-CF.sub.3 -2-pyridinyl                                                       S                  CH.sub.2 CH.sub.2                                        CH═CH CH(Me)CH.sub.2                                                      C(Me)═CH CH.sub.2 CH(Me)                                                  CH═C(Me) CH(Me)CH(Me)                                                     C(Me)═C(Me) CH.sub.2 O                                                    S(O).sub.2 CH═C(Cl)C(═O)O                                             CH.sub.2 O--N═C(CN) CH═N--O--CH.sub.2                                 CH.sub.2 O--N═C(c-Pr) CH═N--O--CH(Me)                                 CH.sub.2 O--N═C(CN)C(═O) CH.sub.2 O--N═C(Et)                      CH.sub.2 O--N═C(NHMe) CH.sub.2 O--N═C(NH.sub.2)                       CH.sub.2 O--N(Me)C(═O)N(Me) CH.sub.2 O--N(Me)C(═S)N(Me)                                     CH.sub.2 SC(SMe)═N CH═N--N(Me)                  CH.sub.2 OC(═O)O CH.sub.2 OC(═S)O                                     CH.sub.2 SC(═O)N(Me) CH.sub.2 SC(═O)NH                                CH.sub.2 SC(═O)O CH.sub.2 SC(═S)O                                     CH.sub.2 SC(═NMe)S CH.sub.2 N(Me)C(═O)N(Me)                           CH.sub.2 O--N═C(Me)CH.sub.2 S CH.sub.2 O--N═C(SMe)CH.sub.2 S                                O--N═CH O--N═C(Me)                              S(O) CH.sub.2 SC(Et)═N                                                    CH(Me)O SCH.sub.2                                                             OCH.sub.2 SCH(Me)                                                             OCH(Me) CH.sub.2 O--N═CH                                                  CH.sub.2 S                                                                    CH(Me)S CH═N--O                                                           O C(═O)                                                                   CH.sub.2 OC(═O)NH CH.sub.2 O--N═C(SMe)                                CH.sub.2 O--N═C(OMe) N═C(Cl)C(═O)O                                CH.sub.2 O--N═C(Cl) CH.sub.2 O--N═C(CF.sub.3)                         CH.sub.2 OC(═S)NH CH.sub.2 OC(═S)N(Me)                                CH.sub.2 O--N═C(Me)N(Me) CH.sub.2 O--N═C(Me)OCH.sub.2                 CH.sub.2 O--N═C(Me)N═N CH.sub.2 N(Me)--N═C(Me)                    CH.sub.2 OC(═O)S CH.sub.2 OC(═S)S                                     CH.sub.2 SC(═S)N(Me) CH.sub.2 SC(═S)S                                 CH.sub.2 SC(═O)S CH.sub.2 O--N═C(SMe)CH.sub.2 O                       CH.sub.2 O--N═C(Me)CH.sub.2 O CH.sub.2 OC(Me)═C(CN)                   OCH.sub.2 CH.sub.2 O--N═C(Me) C(Me)═N--O                              CH═N--N═C(Me) C.tbd.C                                                 C.tbd.C--C(═O)O CH.sub.2 SC(c-Pr)═N                                 ______________________________________                                    

                  TABLE 7                                                         ______________________________________                                        Compounds of the Formula I defined as:                                           -                                                                            #STR94##                                                                       - Z                Z                                                       ______________________________________                                        2-Br-Ph           PhCH═CHCH.sub.2                                           2-CN-Ph 2-Me-Ph                                                               2,4-diCl-Ph 2-F-Ph                                                            2-CF.sub.3 -Ph 2-Me-4-Cl-Ph                                                   2-I-Ph 4-Ph-Ph                                                                c-hexyl 3-(2-Cl-PhO)-Ph                                                       4-NO.sub.2 -Ph 3,5-diCl-Ph                                                    PhCH.sub.2 CH.sub.2 3,5-diCF.sub.3 -Ph                                        (2-CN-Ph)CH.sub.2 2-MeO-Ph                                                    CF.sub.3 CH.sub.2 2,6-diMeO-Ph                                                2-MeS-Ph 3-(2-CN-PhO)-Ph                                                      2-CF.sub.3 O-Ph 5-PhO-3-pyridinyl                                             4-Me-Ph 6-Me-2-pyridinyl                                                      4-Cl-Ph 3-CF.sub.3 O-Ph                                                       3-Me-Ph 4-Br-Ph                                                                3-Et-Ph                                                                      3-Cl-2-Me-Ph 4-MeO-Ph                                                         3-t-Bu-Ph 4-t-Bu-Ph                                                           3-F-Ph 4-CN-Ph                                                                4-CF.sub.3 -Ph 4-NO.sub.2 -Ph                                                 3,4-diCl-Ph 4-F-Ph                                                            3,4-diCF.sub.3 -Ph 3-Ph-Ph                                                    3-EtO-Ph 3,4-diMe-Ph                                                          Ph 3,5-diMe-Ph                                                                2-nap 3-MeS-Ph                                                                3-SF.sub.5 -Ph                                                                t-Bu 4-Me.sub.3 Si-Ph                                                         4-F-3-CF.sub.3 -Ph 3-Me.sub.3 Ge-Ph                                           5-F-3-CF.sub.3 -Ph 4-Me.sub.3 Ge-Ph                                           PhC.tbd.CCH2 4-PhO-2-pyridinyl                                                2-Et-Ph 6-(2-CN-PhO)-4-pyrimidinyl                                            2-Cl-Ph 6-PhO-4-pyrimidinyol                                                  2,4,6-triCl-Ph 4-EtO-2-pyrimidinyl                                            3-PhO-Ph 3-(4-pyrimidinyloxy)-Ph                                              3-(2-Et-PhO)-Ph 4-(2-thienyl)Ph                                               6-Ph-2-pyridinyl 3-(2-pyridinyloxy)Ph                                         6-PhO-4-pyridinyl 4-(3-Cl-2-pyridinyloxy)-Ph                                  3-thienyloxy-Ph 5-PhO-2-pyrimidinyl                                           3-(4-CF.sub.3 -PhO)-Ph 6-(2-NO.sub.2 -PhO)-4-pyrimidinyl                      3-(2-Me-PhO)-Ph 6-(2-Cl-PhO)-4-pyrimidinyl                                    5-PbO-2-pyridinyl 6-(2-CF.sub.3 -PhO)-4-pyrimidinyl                           6-PhO-2-pyridinyl 4,6-diMeO-2-pyrimidinyl                                     6-CF.sub.3 -2-pyridinyl 4,6-diMe-2-pyrimidinyl                                6-PhO-3-pyridinyl 6-CF.sub.3 -4-pyrimidinyl                                   2-pyrimidinyl                                                                 4-pyrimidinyl 4-CF.sub.3 -2-pyrimidinyl                                       4-MeO-2-pyrimidinyl 6-CF.sub.3 -2-pyrazinyl                                   4-Me-2-pyrimidinyl 5-CF.sub.3 -3-pyridinyl                                    6-MeO-4-pyrimidinyl 3-MeO-2-pyridinyl                                         2-Ph-4-thiazolyl 5-CN-2-pyridinyl                                             3-MeO-6-pyridazinyl 6-Me-2-pyridinyl                                          5-Me-2-furanyl 4-t-Bu-2-nap                                                   2,5-diMe-3-thienyl 3,5-diBr-Ph                                                3-OCF.sub.2 H-Ph 4-t-Bu-2-pyridinyl                                           4-OCF.sub.2 H-Ph 4-Ph-2-pyridinyl                                             5-Me-2-nap 4-Me.sub.3 Si-2-pyridinyl                                          6-Me.sub.3 Si-2-nap 5-Me.sub.3 Ge-2-pyridinyl                                 7-OCF.sub.3 -2-nap 4-CF.sub.3 -2-nap                                        ______________________________________                                    

                  TABLE 8                                                         ______________________________________                                        Compounds of the Formula I defined as:                                           -                                                                            #STR95##                                                                       - Z                Z                                                       ______________________________________                                        2-Br-Ph           PhCH═CHCH.sub.2                                           2-CN-Ph 2-Me-Ph                                                               2,4-diCl-Ph 2-F-Ph                                                            2-CF.sub.3 -Ph 2-Me-4-Cl-Ph                                                   2-I-Ph 4-Ph-Ph                                                                c-hexyl 3-(2-Cl-PhO)-Ph                                                       4-NO.sub.2 -Ph 3,5-diCl-Ph                                                    PhCH.sub.2 CH.sub.2 3,5-diCF.sub.3 -Ph                                        (2-CN-Ph)CH.sub.2 2-MeO-Ph                                                    CF.sub.3 CH.sub.2 2,6-diMeO-Ph                                                2-MeS-Ph 3-(2-CN-PhO)-Ph                                                      2-CF.sub.3 O-Ph 5-PhO-3-pyridinyl                                             4-Me-Ph 6-Me-2-pyridinyl                                                      4-Cl-Ph 3-CF.sub.3 O-Ph                                                       3-Me-Ph 4-Br-Ph                                                               3-CF.sub.3 -Ph 3-Et-Ph                                                        3-Cl-2-Me-Ph 4-MeO-Ph                                                         3-t-Bu-Ph 4-t-Bu-Ph                                                           3-F-Ph 4-CN-Ph                                                                4-CF.sub.3 -Ph 4-NO.sub.2 -Ph                                                 3,4-diCl-Ph 4-F-Ph                                                            3,4-diCF.sub.3 -Ph 3-Ph-Ph                                                    3-EtO-Ph 3,4-diMe-Ph                                                          Ph 3,5-diMe-Ph                                                                2-nap 3-MeS-Ph                                                                3-SF.sub.5 -Ph 3-Me.sub.3 Si-Ph                                               t-Bu 4-Me.sub.3 Si-Ph                                                         4-F-3-CF.sub.3 -Ph 3-Me.sub.3 Ge-Ph                                           5-F-3-CF.sub.3 -Ph 4-Me.sub.3 Ge-Ph                                           PhC.tbd.CCH2 4-PhO-2-pyridinyl                                                2-Et-Ph 6-(2-CN-PhO)-4-pyrimidinyl                                            2-Cl-Ph 6-PhO-4-pyrimidinyol                                                  2,4,6-triCl-Ph 4-EtO-2-pyrimidinyl                                            3-PhO-Ph 3-(4-pyrimidinyloxy)-Ph                                              3-(2-Et-PhO)-Ph 4-(2-thienyl)Ph                                               6-Ph-2-pyridinyl 3-(2-pyridinyloxy)Ph                                         6-PhO-4-pyridinyl 4-(3-Cl-2-pyridinyloxy)-Ph                                  3-thienyloxy-Ph 5-PhO-2-pyrimidinyl                                           3-(4-CF.sub.3 -PhO)-Ph 6-(2-NO.sub.2 -PhO)-4-pyrimidinyl                      3-(2-Me-PhO)-Ph 6-(2-Cl-PhO)-4-pyrimidinyl                                    5-PbO-2-pyridinyl 6-(2-CF.sub.3 -PhO)-4-pyrimidinyl                           6-PhO-2-pyridinyl 4,6-diMeO-2-pyrimidinyl                                     6-CF.sub.3 -2-pyridinyl 4,6-diMe-2-pyrimidinyl                                6-PhO-3-pyridinyl 6-CF.sub.3 -4-pyrimidinyl                                   2-pyrimidinyl 4-CF.sub.3 -2-pyridinyl                                         4-pyrimidinyl 4-CF.sub.3 -2-pyrimidinyl                                       4-MeO-2-pyrimidinyl 6-CF.sub.3 -2-pyrazinyl                                   4-Me-2-pyrimidinyl 5-CF.sub.3 -3-pyridinyl                                    6-MeO-4-pyrimidinyl 3-MeO-2-pyridinyl                                         2-Ph-4-thiazolyl 5-CN-2-pyridinyl                                             3-MeO-6-pyridazinyl 6-Me-2-pyridinyl                                          5-Me-2-furanyl 4-t-Bu-2-nap                                                   2,5-diMe-3-thienyl 3,5-diBr-Ph                                                3-OCF.sub.2 H-Ph 4-t-Bu-2-pyridinyl                                           4-OCF.sub.2 H-Ph 4-Ph-2-pyridinyl                                             5-Me-2-nap 4-Me.sub.3 Si-2-pyridinyl                                          6-Me.sub.3 Si-2-nap 5-Me.sub.3 Ge-2-pyridinyl                                 7-OCF.sub.3 -2-nap 4-CF.sub.3 -2-nap                                        ______________________________________                                    

                  TABLE 9                                                         ______________________________________                                        Compounds of the Formula I defined as:                                           -                                                                            #STR96##                                                                       - Z                Z                                                       ______________________________________                                        2-Br-Ph           PhCH═CHCH.sub.2                                           2-CN-Ph 2-Me-Ph                                                               2,4-diCl-Ph 2-F-Ph                                                            2-CF.sub.3 -Ph 2-Me-4-Cl-Ph                                                   2-I-Ph 4-Ph-Ph                                                                c-hexyl 3-(2-Cl-PhO)-Ph                                                       4-NO.sub.2 -Ph 3,5-diCl-Ph                                                    PhCH.sub.2 CH.sub.2 3,5-diCF.sub.3 -Ph                                        (2-CN-Ph)CH.sub.2 2-MeO-Ph                                                    CF.sub.3 CH.sub.2 2,6-diMeO-Ph                                                2-MeS-Ph 3-(2-CN-PhO)-Ph                                                      2-CF.sub.3 O-Ph 5-PhO-3-pyridinyl                                             4-Me-Ph 6-Me-2-pyridinyl                                                      4-Cl-Ph 3-CF.sub.3 O-Ph                                                       3-Me-Ph 4-Br-Ph                                                               3-CF.sub.3 -Ph 3-Et-Ph                                                        3-Cl-2-Me-Ph 4-MeO-Ph                                                         3-t-Bu-Ph 4-t-Bu-Ph                                                           3-F-Ph 4-CN-Ph                                                                4-CF.sub.3 -Ph 4-NO.sub.2 -Ph                                                 3,4-diCl-Ph 4-F-Ph                                                            3,4-diCF.sub.3 -Ph 3-Ph-Ph                                                    3-EtO-Ph 3,4-diMe-Ph                                                          Ph 3,5-diMe-Ph                                                                2-nap 3-MeS-Ph                                                                3-SF.sub.5 -Ph 3-Me.sub.3 Si-Ph                                               t-Bu 4-Me.sub.3 Si-Ph                                                         4-F-3-CF.sub.3 -Ph 3-Me.sub.3 Ge-Ph                                           5-F-3-CF.sub.3 -Ph 4-Me.sub.3 Ge-Ph                                           PhC.tbd.CCH2 4-PhO-2-pyridinyl                                                2-Et-Ph 6-(2-CN-PhO)-4-pyrimidinyl                                            2-Cl-Ph 6-PhO-4-pyrimidinyl                                                   2,4,6-triCl-Ph 4-EtO-2-pyrimidinyl                                            3-PhO-Ph 3-(4-pyrimidinyloxy)-Ph                                              3-(2-Et-PhO)-Ph 4-(2-thienyl)Ph                                               6-Ph-2-pyridinyl 3-(2-pyridinyloxy)Ph                                         6-PhO-4-pyridinyl 4-(3-Cl-2-pyridinyloxy)-Ph                                  3-thienyloxy-Ph 5-PhO-2-pyrimidinyl                                           3-(4-CF.sub.3 -PhO)-Ph 6-(2-NO.sub.2 -PhO)-4-pyrimidinyl                      3-(2-Me-PhO)-Ph 6-(2-Cl-PhO)-4-pyrimidinyl                                    5-PbO-2-pyridinyl 6-(2-CF.sub.3 -PhO)-4-pyrimidinyl                           6-PhO-2-pyridinyl 4,6-diMeO-2-pyrimidinyl                                     6-CF.sub.3 -2-pyridinyl 4,6-diMe-2-pyrimidinyl                                6-PhO-3-pyridinyl 6-CF.sub.3 -4-pyrimidinyl                                   2-pyrimidinyl 4-CF.sub.3 -2-pyridinyl                                         4-pyrimidinyl 4-CF.sub.3 -2-pyrimidinyl                                       4-MeO-2-pyrdimidinyl 6-CF.sub.3 -2-pyrazinyl                                  4-Me-2-pyrimidinyl 5-CF.sub.3 -3-pyridinyl                                    6-MeO-4-pyrimidinyl 3-MeO-2-pyridinyl                                         2-Ph-4-thiazolyl 5-CN-2-pyridinyl                                             3-MeO-6-pyridazinyl 6-Me-2-pyridinyl                                          5-Me-2-furanyl 4-t-Bu-2-nap                                                   2,5-diMe-3-thienyl 3,5-diBr-Ph                                                3-OCF.sub.2 H-Ph 4-t-Bu-2-pyridinyl                                           4-OCF.sub.2 H-Ph 4-Ph-2-pyridinyl                                             5-Me-2-nap 4-Me.sub.3 Si-2-pyridinyl                                          6-Me.sub.3 Si-2-nap 5-Me.sub.3 Ge-2-pyridinyl                                 7-OCF.sub.3 -2-nap 4-CF.sub.3 -2-nap                                        ______________________________________                                    

                  TABLE 10                                                        ______________________________________                                        Compounds of the Formula I defined as:                                           -                                                                            #STR97##                                                                       - Z                Z                                                       ______________________________________                                        2-Br-Ph           PhCH═CHCH.sub.2                                           2-CN-Ph 2-Me-Ph                                                               2,4-diCl-Ph 2-F-Ph                                                            2-CF.sub.3 -Ph 2-Me-4-Cl-Ph                                                   2-I-Ph 4-Ph-Ph                                                                c-hexyl 3-(2-Cl-PhO)-Ph                                                       4-NO.sub.2 -Ph 3,5-diCl-Ph                                                    PhCH.sub.2 CH.sub.2 3,5-diCF.sub.3 -Ph                                        (2-CN-Ph)CH.sub.2 2-MeO-Ph                                                    CF.sub.3 CH.sub.2 2,6-diMeO-Ph                                                2-MeS-Ph 3-(2-CN-PhO)-Ph                                                      2-CF.sub.3 O-Ph 5-PhO-3-pyridinyl                                             4-Me-Ph 6-Me-2-pyridinyl                                                      4-Cl-Ph 3-CF.sub.3 O-Ph                                                       3-Me-Ph 4-Br-Ph                                                                3-Et-Ph                                                                      3-Cl-2-Me-Ph 4-MeO-Ph                                                         3-t-Bu-Ph 4-t-Bu-Ph                                                           3-F-Ph 4-CN-Ph                                                                4-CF.sub.3 -Ph 4-NO.sub.2 -Ph                                                 3,4-diCl-Ph 4-F-Ph                                                            3,4-diCF.sub.3 -Ph 3-Ph-Ph                                                    3-EtO-Ph 3,4-diMe-Ph                                                          Ph 3,5-diMe-Ph                                                                2-nap 3-MeS-Ph                                                                3-SF.sub.5 -Ph                                                                t-Bu 4-Me.sub.3 Si-Ph                                                         4-F-3-CF.sub.3 -Ph 3-Me.sub.3 Ge-Ph                                           5-F-3-CF.sub.3 -Ph 4-Me.sub.3 Ge-Ph                                           PhC.tbd.CCH2 4-PhO-2-pyridinyl                                                2-Et-Ph 6-(2-CN-PhO)-4-pyrimidinyl                                            2-Cl-Ph 6-PhO-4-pyrimidinyl                                                   2,4,6-triCl-Ph 4-EtO-2-pyrimidinyl                                            3-PhO-Ph 3-(4-pyrimidinyloxy)-Ph                                              3-(2-Et-PhO)-Ph 4-(2-thienyl)Ph                                               6-Ph-2-pyridinyl 3-(2-pyridinyloxy)Ph                                         6-PhO-4-pyridinyl 4-(3-Cl-2-pyridinyloxy)-Ph                                  3-thienyloxy-Ph 5-PhO-2-pyrimidinyl                                           3-(4-CF.sub.3 -PhO)-Ph 6-(2-NO.sub.2 -PhO)-4-pyrimidinyl                      3-(2-Me-PhO)-Ph 6-(2-Cl-PhO)-4-pyrimidinyl                                    5-PbO-2-pyridinyl 6-(2-CF.sub.3 -PhO)-4-pyrimidinyl                           6-PhO-2-pyridinyl 4,6-diMeO-2-pyrimidinyl                                     6-CF.sub.3 -2-pyridinyl 4,6-diMe-2-pyrimidinyl                                6-PhO-3-pyridinyl 6-CF.sub.3 -4-pyrimidinyl                                   2-pyrimidinyl                                                                 4-pyrimidinyl 4-CF.sub.3 -2-pyrimidinyl                                       4-MeO-2-pyrdimidinyl 6-CF.sub.3 -2-pyrazinyl                                  4-Me-2-pyrimidinyl 5-CF.sub.3 -3-pyridinyl                                    6-MeO-4-pyrimidinyl 3-MeO-2-pyridinyl                                         2-Ph-4-thiazolyl 5-CN-2-pyridinyl                                             3-MeO-6-pyridazinyl 6-Me-2-pyridinyl                                          5-Me-2-furanyl 4-t-Bu-2-nap                                                   2,5-diMe-3-thienyl 3,5-diBr-Ph                                                3-OCF.sub.2 H-Ph 4-t-Bu-2-pyridinyl                                           4-OCF.sub.2 H-Ph 4-Ph-2-pyridinyl                                             5-Me-2-nap 4-Me.sub.3 Si-2-pyridinyl                                          6-Me.sub.3 Si-2-nap 5-Me.sub.3 Ge-2-pyridinyl                                 7-OCF.sub.3 -2-nap 4-CF.sub.3 -2-nap                                        ______________________________________                                    

                  TABLE 11                                                        ______________________________________                                        Compounds of the Formula I defined as:                                           -                                                                            #STR98##                                                                       - Z                Z                                                       ______________________________________                                        2-Br-Ph           PhCH═CHCH.sub.2                                           2-CN-Ph 2-Me-Ph                                                               2,4-diCl-Ph 2-F-Ph                                                            2-CF.sub.3 -Ph 2-Me-4-Cl-Ph                                                   2-I-Ph 4-Ph-Ph                                                                c-hexyl 3-(2-Cl-PhO)-Ph                                                       4-NO.sub.2 -Ph 3,5-diCl-Ph                                                    PhCH.sub.2 CH.sub.2 3,5-diCF.sub.3 -Ph                                        (2-CN-Ph)CH.sub.2 2-MeO-Ph                                                    CF.sub.3 CH.sub.2 2,6-diMeO-Ph                                                2-MeS-Ph 3-(2-CN-PhO)-Ph                                                      2-CF.sub.3 O-Ph 5-PhO-3-pyridinyl                                             4-Me-Ph 6-Me-2-pyridinyl                                                      4-Cl-Ph 3-CF.sub.3 O-Ph                                                       3-Me-Ph 4-Br-Ph                                                                3-Et-Ph                                                                      3-Cl-2-Me-Ph 4-MeO-Ph                                                         3-t-Bu-Ph 4-t-Bu-Ph                                                           3-F-Ph 4-CN-Ph                                                                4-CF.sub.3 -Ph 4-NO.sub.2 -Ph                                                 3,4-diCl-Ph 4-F-Ph                                                            3,4-diCF.sub.3 -Ph 3-Ph-Ph                                                    3-EtO-Ph 3,4-diMe-Ph                                                          Ph 3,5-diMe-Ph                                                                2-nap 3-MeS-Ph                                                                3-SF.sub.5 -Ph                                                                t-Bu 4-Me.sub.3 Si-Ph                                                         4-F-3-CF.sub.3 -Ph 3-Me.sub.3 Ge-Ph                                           5-F-3-CF.sub.3 -Ph 4-Me.sub.3 Ge-Ph                                           PhC.tbd. CCH2 4-PhO-2-pyridinyl                                               2-Et-Ph 6-(2-CN-PhO)-4-pyrimidinyl                                            2-Cl-Ph 6-PhO-4-pyrimidinyl                                                   2,4,6-triCl-Ph 4-EtO-2-pyrimidinyl                                            3-PhO-Ph 3-(4-pyrimidinyloxy)-Ph                                              3-(2-Et-PhO)-Ph 4-(2-thienyl)Ph                                               6-Ph-2-pyridinyl 3-(2-pyridinyloxy)Ph                                         6-PhO-4-pyridinyl 4-(3-Cl-2-pyridinyloxy)-Ph                                  3-thienyloxy-Ph 5-PhO-2-pyrimidinyl                                           3-(4-CF.sub.3 -PhO)-Ph 6-(2-NO.sub.2 -PhO)-4-pyrimidinyl                      3-(2-Me-PhO)-Ph 6-(2-Cl-PhO)-4-pyrimidinyl                                    5-PbO-2-pyridinyl 6-(2-CF.sub.3 -PhO)-4-pyrimidinyl                           6-PhO-2-pyridinyl 4,6-diMeO-2-pyrimidinyl                                     6-CF.sub.3 -2-pyridinyl 4,6-diMe-2-pyrimidinyl                                6-PhO-3-pyridinyl 6-CF.sub.3 -4-pyrimidinyl                                   2-pyrimidinyl                                                                 4-pyrimidinyl 4-CF.sub.3 -2-pyrimidinyl                                       4-MeO-2-pyrdimidinyl 6-CF.sub.3 -2-pyrazinyl                                  4-Me-2-pyrimidinyl 5-CF.sub.3 -3-pyridinyl                                    6-MeO-4-pyrimidinyl 3-MeO-2-pyridinyl                                         2-Ph-4-thiazolyl 5-CN-2-pyridinyl                                             3-MeO-6-pyridazinyl 6-Me-2-pyridinyl                                          5-Me-2-furanyl 4-t-Bu-2-nap                                                   2,5-diMe-3-thienyl 3,5-diBr-Ph                                                3-OCF.sub.2 H-Ph 4-t-Bu-2-pyridinyl                                           4-OCF.sub.2 H-Ph 4-Ph-2-pyridinyl                                             5-Me-2-nap 4-Me.sub.3 Si-2-pyridinyl                                          6-Me.sub.3 Si-2-nap 5-Me.sub.3 Ge-2-pyridinyl                                 7-OCF.sub.3 -2-nap 4-CF.sub.3 -2-nap                                        ______________________________________                                    

                  TABLE 12                                                        ______________________________________                                        Compounds of the Formula I defined as:                                           -                                                                            #STR99##                                                                       - Z                Z                                                       ______________________________________                                        2-Br-Ph           PhCH═CHCH.sub.2                                           2-CN-Ph 2-Me-Ph                                                               2,4-diCl-Ph 2-F-Ph                                                            2-CF.sub.3 -Ph 2-Me-4-Cl-Ph                                                   2-I-Ph 4-Ph-Ph                                                                c-hexyl 3-(2-Cl-PhO)-Ph                                                       4-NO.sub.2 -Ph 3,5-diCl-Ph                                                    PhCH.sub.2 CH.sub.2 3,5-diCF.sub.3 -Ph                                        (2-CN-Ph)CH.sub.2 2-MeO-Ph                                                    CF.sub.3 CH.sub.2 2,6-diMeO-Ph                                                2-MeS-Ph 3-(2-CN-PhO)-Ph                                                      2-CF.sub.3 O-Ph 5-PhO-3-pyridinyl                                             4-Me-Ph 6-Me-2-pyridinyl                                                      4-Cl-Ph 3-CF.sub.3 O-Ph                                                       3-Me-Ph 4-Br-Ph                                                                3-Et-Ph                                                                      3-Cl-2-Me-Ph 4-MeO-Ph                                                         3-t-Bu-Ph 4-t-Bu-Ph                                                           3-F-Ph 4-CN-Ph                                                                4-CF.sub.3 -Ph 4-NO.sub.2 -Ph                                                 3,4-diCl-Ph 4-F-Ph                                                            3,4-diCF.sub.3 -Ph 3-Ph-Ph                                                    3-EtO-Ph 3,4-diMe-Ph                                                          Ph 3,5-diMe-Ph                                                                2-nap 3-MeS-Ph                                                                3-SF.sub.5 -Ph 3-Me.sub.3 Si-Ph                                               t-Bu 4-Me.sub.3 Si-Ph                                                         4-F-3-CF.sub.3 -Ph 3-Me.sub.3 Ge-Ph                                           5-F-3-CF.sub.3 -Ph 4-Me.sub.3 Ge-Ph                                           PhC.tbd.CCH2 4-PhO-2-pyridinyl                                                2-Et-Ph 6-(2-CN-PhO)-4-pyrimidinyl                                            2-Cl-Ph 6-PhO-4-pyrimidinyl                                                   2,4,6-triCl-Ph 4-EtO-2-pyrimidinyl                                            3-PhO-Ph 3-(4-pyrimidinyloxy)-Ph                                              3-(2-Et-PhO)-Ph 4-(2-thienyl)Ph                                               6-Ph-2-pyridinyl 3-(2-pyridinyloxy)Ph                                         6-PhO-4-pyridinyl 4-(3-Cl-2-pyridinyloxy)-Ph                                  3-thienyloxy-Ph 5-PhO-2-pyrimidinyl                                           3-(4-CF.sub.3 -PhO)-Ph 6-(2-NO.sub.2 -PhO)-4-pyrimidinyl                      3-(2-Me-PhO)-Ph 6-(2-Cl-PhO)-4-pyrimidinyl                                    5-PbO-2-pyridinyl 6-(2-CF.sub.3 -PhO)-4-pyrimidinyl                           6-PhO-2-pyridinyl 4,6-diMeO-2-pyrimidinyl                                     6-CF.sub.3 -2-pyridinyl 4,6-diMe-2-pyrimidinyl                                6-PhO-3-pyridinyl 6-CF.sub.3 -4-pyrimidinyl                                   2-pyrimidinyl 4-CF.sub.3 -2-pyridinyl                                         4-pyrimidinyl 4-CF.sub.3 -2-pyrimidinyl                                       4-MeO-2-pyrdimidinyl 6-CF.sub.3 -2-pyrazinyl                                  4-Me-2-pyrimidinyl 5-CF.sub.3 -3-pyridinyl                                    6-MeO-4-pyrimidinyl 3-MeO-2-pyridinyl                                         2-Ph-4-thiazolyl 5-CN-2-pyridinyl                                             3-MeO-6-pyridazinyl 6-Me-2-pyridinyl                                          5-Me-2-furanyl 4-t-Bu-2-nap                                                   2,5-diMe-3-thienyl 3,5-diBr-Ph                                                3-OCF.sub.2 H-Ph 4-t-Bu-2-pyridinyl                                           4-OCF.sub.2 H-Ph 4-Ph-2-pyridinyl                                             5-Me-2-nap 4-Me.sub.3 Si-2-pyridinyl                                          6-Me.sub.3 Si-2-nap 5-Me.sub.3 Ge-2-pyridinyl                                 7-OCF.sub.3 -2-nap 4-CF.sub.3 -2-nap                                        ______________________________________                                    

                  TABLE 13                                                        ______________________________________                                        Compounds of the Formula I defined as:                                           -                                                                            #STR100##                                                                      - Z                Z                                                       ______________________________________                                        2-Br-Ph           PhCH═CHCH.sub.2                                           2-CN-Ph 2-Me-Ph                                                               2,4-diCl-Ph 2-F-Ph                                                            2-CF.sub.3 -Ph 2-Me-4-Cl-Ph                                                   2-I-Ph 4-Ph-Ph                                                                c-hexyl 3-(2-Cl-PhO)-Ph                                                       4-NO.sub.2 -Ph 3,5-diCl-Ph                                                    PhCH.sub.2 CH.sub.2 3,5-diCF.sub.3 -Ph                                        (2-CN-Ph)CH.sub.2 2-MeO-Ph                                                    CF.sub.3 CH.sub.2 2,6-diMeO-Ph                                                2-MeS-Ph 3-(2-CN-PhO)-Ph                                                      2-CF.sub.3 O-Ph 5-PhO-3-pyridinyl                                             4-Me-Ph 6-Me-2-pyridinyl                                                      4-Cl-Ph 3-CF.sub.3 O-Ph                                                       3-Me-Ph 4-Br-Ph                                                               3-CF.sub.3 -Ph 3-Et-Ph                                                        3-Cl-2-Me-Ph 4-MeO-Ph                                                         3-t-Bu-Ph 4-t-Bu-Ph                                                           3-F-Ph 4-CN-Ph                                                                4-CF.sub.3 -Ph 4-NO.sub.2 -Ph                                                 3,4-diCl-Ph 4-F-Ph                                                            3,4-diCF.sub.3 -Ph 3-Ph-Ph                                                    3-EtO-Ph 3,4-diMe-Ph                                                          Ph 3,5-diMe-Ph                                                                2-nap 3-MeS-Ph                                                                3-SF.sub.5 -Ph 3-Me.sub.3 Si-Ph                                               t-Bu 4-Me.sub.3 Si-Ph                                                         4-F-3-CF.sub.3 -Ph 3-Me.sub.3 Ge-Ph                                           5-F-3-CF.sub.3 -Ph 4-Me.sub.3 Ge-Ph                                           PhC.tbd.CCH2 4-PhO-2-pyridinyl                                                2-Et-Ph 6-(2-CN-PhO)-4-pyrimidinyl                                            2-Cl-Ph 6-PhO-4-pyrimidinyl                                                   2,4,6-triCl-Ph 4-EtO-2-pyrimidinyl                                            3-PhO-Ph 3-(4-pyrimidinyloxy)-Ph                                              3-(2-Et-PhO)-Ph 4-(2-thienyl)Ph                                               6-Ph-2-pyridinyl 3-(2-pyridinyloxy)Ph                                         6-PhO-4-pyridinyl 4-(3-Cl-2-pyridinyloxy)-Ph                                  3-thienyloxy-Ph 5-PhO-2-pyrimidinyl                                           3-(4-CF.sub.3 -PhO)-Ph 6-(2-NO.sub.2 -PhO)-4-pyrimidinyl                      3-(2-Me-PhO)-Ph 6-(2-Cl-PhO)-4-pyrimidinyl                                    5-PbO-2-pyridinyl 6-(2-CF.sub.3 -PhO)-4-pyrimidinyl                           6-PhO-2-pyridinyl 4,6-diMeO-2-pyrimidinyl                                     6-CF.sub.3 -2-pyridinyl 4,6-diMe-2-pyrimidinyl                                6-PhO-3-pyridinyl 6-CF.sub.3 -4-pyrimidinyl                                   2-pyrimidinyl 4-CF.sub.3 -2-pyridinyl                                         4-pyrimidinyl 4-CF.sub.3 -2-pyrimidinyl                                       4-MeO-2-pyrdimidinyl 6-CF.sub.3 -2-pyrazinyl                                  4-Me-2-pyrimidinyl 5-CF.sub.3 -3-pyridinyl                                    6-MeO-4-pyrimidinyl 3-MeO-2-pyridinyl                                         2-Ph-4-thiazolyl 5-CN-2-pyridinyl                                             3-MeO-6-pyridazinyl 6-Me-2-pyridinyl                                          5-Me-2-furanyl 4-t-Bu-2-nap                                                   2,5-diMe-3-thienyl 3,5-diBr-Ph                                                3-OCF.sub.2 H-Ph 4-t-Bu-2-pyridinyl                                           4-OCF.sub.2 H-Ph 4-Ph-2-pyridinyl                                             5-Me-2-nap 4-Me.sub.3 Si-2-pyridinyl                                          6-Me.sub.3 Si-2-nap 5-Me.sub.3 Ge-2-pyridinyl                                 7-OCF.sub.3 -2-nap 4-CF.sub.3 -2-nap                                        ______________________________________                                    

                  TABLE 14                                                        ______________________________________                                        Compounds of the Formula I defined as:                                           -                                                                            #STR101##                                                                      - Z                Z                                                       ______________________________________                                        2-Br-Ph           PhCH═CHCH.sub.2                                           2-CN-Ph 2-Me-Ph                                                               2,4-diCl-Ph 2-F-Ph                                                            2-CF.sub.3 -Ph 2-Me-4-Cl-Ph                                                   2-I-Ph 4-Ph-Ph                                                                c-hexyl 3-(2-Cl-PhO)-Ph                                                       4-NO.sub.2 -Ph 3,5-diCl-Ph                                                    PhCH.sub.2 CH.sub.2 3,5-diCF.sub.3 -Ph                                        (2-CN-Ph)CH.sub.2 2-MeO-Ph                                                    CF.sub.3 CH.sub.2 2,6-diMeO-Ph                                                2-MeS-Ph 3-(2-CN-PhO)-Ph                                                      2-CF.sub.3 O-Ph 5-PhO-3-pyridinyl                                             4-Me-Ph 6-Me-2-pyridinyl                                                      4-Cl-Ph 3-CF.sub.3 O-Ph                                                       3-Me-Ph 4-Br-Ph                                                                3-Et-Ph                                                                      3-Cl-2-Me-Ph 4-MeO-Ph                                                         3-t-Bu-Ph 4-t-Bu-Ph                                                           3-F-Ph 4-CN-Ph                                                                4-CF.sub.3 -Ph 4-NO.sub.2 -Ph                                                 3,4-diCl-Ph 4-F-Ph                                                            3,4-diCF.sub.3 -Ph 3-Ph-Ph                                                    3-EtO-Ph 3,4-diMe-Ph                                                          Ph 3,5-diMe-Ph                                                                2-nap 3-MeS-Ph                                                                3-SF.sub.5 -Ph                                                                t-Bu 4-Me.sub.3 Si-Ph                                                         4-F-3-CF.sub.3 -Ph 3-Me.sub.3 Ge-Ph                                           5-F-3-CF.sub.3 -Ph 4-Me.sub.3 Ge-Ph                                           PhC.tbd.CCH2 4-PhO-2-pyridinyl                                                2-Et-Ph 6-(2-CN-PhO)-4-pyrimidinyl                                            2-Cl-Ph 6-PhO-4-pyrimidinyl                                                   2,4,6-triCl-Ph 4-EtO-2-pyrimidinyl                                            3-PhO-Ph 3-(4-pyrimidinyloxy)-Ph                                              3-(2-Et-PhO)-Ph 4-(2-thienyl)Ph                                               6-Ph-2-pyridinyl 3-(2-pyridinyloxy)Ph                                         6-PhO-4-pyridinyl 4-(3-Cl-2-pyridinyloxy)-Ph                                  3-thienyloxy-Ph 5-PhO-2-pyrimidinyl                                           3-(4-CF.sub.3 -PhO)-Ph 6-(2-NO.sub.2 -PhO)-4-pyrimidinyl                      3-(2-Me-PhO)-Ph 6-(2-Cl-PhO)-4-pyrimidinyl                                    5-PbO-2-pyridinyl 6-(2-CF.sub.3 -PhO)-4-pyrimidinyl                           6-PhO-2-pyridinyl 4,6-diMeO-2-pyrimidinyl                                     6-CF.sub.3 -2-pyridinyl 4,6-diMe-2-pyrimidinyl                                6-PhO-3-pyridinyl 6-CF.sub.3 -4-pyrimidinyl                                   2-pyrimidinyl                                                                 4-pyrimidinyl 4-CF.sub.3 -2-pyrimidinyl                                       4-MeO-2-pyrdimidinyl 6-CF.sub.3 -2-pyrazinyl                                  4-Me-2-pyrimidinyl 5-CF.sub.3 -3-pyridinyl                                    6-MeO-4-pyrimidinyl 3-MeO-2-pyridinyl                                         2-Ph-4-thiazolyl 5-CN-2-pyridinyl                                             3-MeO-6-pyridazinyl 6-Me-2-pyridinyl                                          5-Me-2-furanyl 4-t-Bu-2-nap                                                   2,5-diMe-3-thienyl 3,5-diBr-Ph                                                3-OCF.sub.2 H-Ph 4-t-Bu-2-pyridinyl                                           4-OCF.sub.2 H-Ph 4-Ph-2-pyridinyl                                             5-Me-2-nap 4-Me.sub.3 Si-2-pyridinyl                                          6-Me.sub.3 Si-2-nap 5-Me.sub.3 Ge-2-pyridinyl                                 7-OCF.sub.3 -2-nap 4-CF.sub.3 -2-nap                                        ______________________________________                                    

                  TABLE 15                                                        ______________________________________                                        Compounds of the Formula I defined as:                                           -                                                                            #STR102##                                                                      - Z                Z                                                       ______________________________________                                        2-Br-Ph           PhCH═CHCH.sub.2                                           2-CN-Ph 2-Me-Ph                                                               2,4-diCl-Ph 2-F-Ph                                                            2-CF.sub.3 -Ph 2-Me-4-Cl-Ph                                                   2-I-Ph 4-Ph-Ph                                                                c-hexyl 3-(2-Cl-PhO)-Ph                                                       4-NO.sub.2 -Ph 3,5-diCl-Ph                                                    PhCH.sub.2 CH.sub.2 3,5-diCF.sub.3 -Ph                                        (2-CN-Ph)CH.sub.2 2-MeO-Ph                                                    CF.sub.3 CH.sub.2 2,6-diMeO-Ph                                                2-MeS-Ph 3-(2-CN-PhO)-Ph                                                      2-CF.sub.3 O-Ph 5-PhO-3-pyridinyl                                             4-Me-Ph 6-Me-2-pyridinyl                                                      4-Cl-Ph 3-CF.sub.3 O-Ph                                                       3-Me-Ph 4-Br-Ph                                                                3-Et-Ph                                                                      3-Cl-2-Me-Ph 4-MeO-Ph                                                         3-t-Bu-Ph 4-t-Bu-Ph                                                           3-F-Ph 4-CN-Ph                                                                4-CF.sub.3 -Ph 4-NO.sub.2 -Ph                                                 3,4-diCl-Ph 4-F-Ph                                                            3,4-diCF.sub.3 -Ph 3-Ph-Ph                                                    3-EtO-Ph 3,4-diMe-Ph                                                          Ph 3,5-diMe-Ph                                                                2-nap 3-MeS-Ph                                                                3-SF.sub.5 -Ph                                                                t-Bu 4-Me.sub.3 Si-Ph                                                         4-F-3-CF.sub.3 -Ph 3-Me.sub.3 Ge-Ph                                           5-F-3-CF.sub.3 -Ph 4-Me.sub.3 Ge-Ph                                           PhC.tbd.CCH2 4-PhO-2-pyridinyl                                                2-Et-Ph 6-(2-CN-PhO)-4-pyrimidinyl                                            2-Cl-Ph 6-PhO-4-pyrimidinyl                                                   2,4,6-triCl-Ph 4-EtO-2-pyrimidinyl                                            3-PhO-Ph 3-(4-pyrimidinyloxy)-Ph                                              3-(2-Et-PhO)-Ph 4-(2-thienyl)Ph                                               6-Ph-2-pyridinyl 3-(2-pyridinyloxy)Ph                                         6-PhO-4-pyridinyl 4-(3-Cl-2-pyridinyloxy)-Ph                                  3-thienyloxy-Ph 5-PhO-2-pyrimidinyl                                           3-(4-CF.sub.3 -PhO)-Ph 6-(2-NO.sub.2 -PhO)-4-pyrimidinyl                      3-(2-Me-PhO)-Ph 6-(2-Cl-PhO)-4-pyrimidinyl                                    5-PbO-2-pyridinyl 6-(2-CF.sub.3 -PhO)-4-pyrimidinyl                           6-PhO-2-pyridinyl 4,6-diMeO-2-pyrimidinyl                                     6-CF.sub.3 -2-pyridinyl 4,6-diMe-2-pyrimidinyl                                6-PhO-3-pyridinyl 6-CF.sub.3 -4-pyrimidinyl                                   2-pyrimidinyl                                                                 4-pyrimidinyl 4-CF.sub.3 -2-pyrimidinyl                                       4-MeO-2-pyrdimidinyl 6-CF.sub.3 -2-pyrazinyl                                  4-Me-2-pyrimidinyl 5-CF.sub.3 -3-pyridinyl                                    6-MeO-4-pyrimidinyl 3-MeO-2-pyridinyl                                         2-Ph-4-thiazolyl 5-CN-2-pyridinyl                                             3-MeO-6-pyridazinyl 6-Me-2-pyridinyl                                          5-Me-2-furanyl 4-t-Bu-2-nap                                                   2,5-diMe-3-thienyl 3,5-diBr-Ph                                                3-OCF.sub.2 H-Ph 4-t-Bu-2-pyridinyl                                           4-OCF.sub.2 H-Ph 4-Ph-2-pyridinyl                                             5-Me-2-nap 4-Me.sub.3 Si-2-pyridinyl                                          6-Me.sub.3 Si-2-nap 5-Me.sub.3 Ge-2-pyridinyl                                 7-OCF.sub.3 -2-nap 4-CF.sub.3 -2-nap                                        ______________________________________                                    

                  TABLE 16                                                        ______________________________________                                        Compounds of the Formula I defined as:                                           -                                                                            #STR103##                                                                      - Z                Z                                                       ______________________________________                                        2-Br-Ph           PhCH═CHCH.sub.2                                           2-CN-Ph 2-Me-Ph                                                               2,4-diCl-Ph 2-F-Ph                                                            2-CF.sub.3 -Ph 2-Me-4-Cl-Ph                                                   2-I-Ph 4-Ph-Ph                                                                c-hexyl 3-(2-Cl-PhO)-Ph                                                       4-NO.sub.2 -Ph 3,5-diCl-Ph                                                    PhCH.sub.2 CH.sub.2 3,5-diCF.sub.3 -Ph                                        (2-CN-Ph)CH.sub.2 2-MeO-Ph                                                    CF.sub.3 CH.sub.2 2,6-diMeO-Ph                                                2-MeS-Ph 3-(2-CN-PhO)-Ph                                                      2-CF.sub.3 O-Ph 5-PhO-3-pyridinyl                                             4-Me-Ph 6-Me-2-pyridinyl                                                      4-Cl-Ph 3-CF.sub.3 O-Ph                                                       3-Me-Ph 4-Br-Ph                                                                3-Et-Ph                                                                      3-Cl-2-Me-Ph 4-MeO-Ph                                                         3-t-Bu-Ph 4-t-Bu-Ph                                                           3-F-Ph 4-CN-Ph                                                                4-CF.sub.3 -Ph 4-NO.sub.2 -Ph                                                 3,4-diCl-Ph 4-F-Ph                                                            3,4-diCF.sub.3 -Ph 3-Ph-Ph                                                    3-EtO-Ph 3,4-diMe-Ph                                                          Ph 3,5-diMe-Ph                                                                2-nap 3-MeS-Ph                                                                3-SF.sub.5 -Ph                                                                t-Bu 4-Me.sub.3 Si-Ph                                                         4-F-3-CF.sub.3 -Ph 3-Me.sub.3 Ge-Ph                                           5-F-3-CF.sub.3 -Ph 4-Me.sub.3 Ge-Ph                                           PhC.tbd.CCH2 4-PhO-2-pyridinyl                                                2-Et-Ph 6-(2-CN-PhO)-4-pyrimidinyl                                            2-Cl-Ph 6-PhO-4-pyrimidinyl                                                   2,4,6-triCl-Ph 4-EtO-2-pyrimidinyl                                            3-PhO-Ph 3-(4-pyrimidinyloxy)-Ph                                              3-(2-Et-PhO)-Ph 4-(2-thienyl)Ph                                               6-Ph-2-pyridinyl 3-(2-pyridinyloxy)Ph                                         6-PhO-4-pyridinyl 4-(3-Cl-2-pyridinyloxy)-Ph                                  3-thienyloxy-Ph 5-PhO-2-pyrimidinyl                                           3-(4-CF.sub.3 -PhO)-Ph 6-(2-NO.sub.2 -PhO)-4-pyrimidinyl                      3-(2-Me-PhO)-Ph 6-(2-Cl-PhO)-4-pyrimidinyl                                    5-PbO-2-pyridinyl 6-(2-CF.sub.3 -PhO)-4-pyrimidinyl                           6-PhO-2-pyridinyl 4,6-diMeO-2-pyrimidinyl                                     6-CF.sub.3 -2-pyridinyl 4,6-diMe-2-pyrimidinyl                                6-PhO-3-pyridinyl 6-CF.sub.3 -4-pyrimidinyl                                   2-pyrimidinyl                                                                 4-pyrimidinyl 4-CF.sub.3 -2-pyrimidinyl                                       4-MeO-2-pyrdimidinyl 6-CF.sub.3 -2-pyrazinyl                                  4-Me-2-pyrimidinyl 5-CF.sub.3 -3-pyridinyl                                    6-MeO-4-pyrimidinyl 3-MeO-2-pyridinyl                                         2-Ph-4-thiazolyl 5-CN-2-pyridinyl                                             3-MeO-6-pyridazinyl 6-Me-2-pyridinyl                                          5-Me-2-furanyl 4-t-Bu-2-nap                                                   2,5-diMe-3-thienyl 3,5-diBr-Ph                                                3-OCF.sub.2 H-Ph 4-t-Bu-2-pyridinyl                                           4-OCF.sub.2 H-Ph 4-Ph-2-pyridinyl                                             5-Me-2-nap 4-Me.sub.3 Si-2-pyridinyl                                          6-Me.sub.3 Si-2-nap 5-Me.sub.3 Ge-2-pyridinyl                                 7-OCF.sub.3 -2-nap 4-CF.sub.3 -2-nap                                        ______________________________________                                    

                  TABLE 17                                                        ______________________________________                                        Compounds of Formula I defined as:                                               -                                                                            #STR104##                                                                      -                                                                              X             A       X           A                                       ______________________________________                                        R.sup.2 = Me, W = O                                                                                     MeS         N                                         EtO N EtS N                                                                   n-PrO N n-PrS N                                                               H.sub.2 C═CHCH.sub.2 O N H.sub.2 C═CHCH.sub.2 S N                     HC.tbd.CCH.sub.2 O N HC.tbd.CCH.sub.2 S N                                     CF.sub.3 O N CF.sub.3 S N                                                     (c-Pr)O N (c-Pr)S N                                                           MeO CH MeS CH                                                                 EtO CH EtS CH                                                                 n-PrO CH n-PrS CH                                                             H.sub.2 C═CHCH.sub.2 O CH H.sub.2 C═CHCH.sub.2 S CH                   HC.tbd.CCH.sub.2 O CH HC.tbd.CCH.sub.2 S CH                                   CF.sub.3 O CH CF.sub.3 S CH                                                   (c-Pr)O CH (c-Pr)S CH                                                       R.sup.2 = Et, W = O                                                               MeO           N       MeS         N                                         EtO N EtS N                                                                   n-PrO N n-PrS N                                                               H.sub.2 C═CHCH.sub.2 O N H.sub.2 C═CHCH.sub.2 S N                     HC.tbd.CCH.sub.2 O N HC.tbd.CCH.sub.2 S N                                     CF.sub.3 O N CF.sub.3 S N                                                     (c-Pr)O N (c-Pr)S N                                                           MeO CH MeS CH                                                                 EtO CH EtS CH                                                                 n-PrO CH n-PrS CH                                                             H.sub.2 C═CHCH.sub.2 O CH H.sub.2 C═CHCH.sub.2 S CH                   HC.tbd.CCH.sub.2 O CH HC.tbd.CCH.sub.2 S CH                                   CF.sub.3 O CH CF.sub.3 S CH                                                   (c-Pr)O CH (c-Pr)S CH                                                       R.sup.2 = Me, W = S                                                               MeO           N       MeS         N                                         EtO N EtS N                                                                   n-PrO N n-PrS N                                                               H.sub.2 C═CHCH.sub.2 O N H.sub.2 C═CHCH.sub.2 S N                     HC.tbd.CCH.sub.2 O N HC.tbd.CCH.sub.2 S N                                     CF.sub.3 O N CF.sub.3 S N                                                     (c-Pr)O N (c-Pr)S N                                                           MeO CH MeS CH                                                                 EtO CH EtS CH                                                                 n-PrO CH n-PrS CH                                                             H.sub.2 C═CHCH.sub.2 O CH H.sub.2 C═CHCH.sub.2 S CH                   HC.tbd.CCH.sub.2 O CH HC.tbd.CCH.sub.2 S CH                                   CF.sub.3 O CH CF.sub.3 S CH                                                   (c-Pr)O CH (c-Pr)S CH                                                       R.sup.2 = Et, W = S                                                               MeO           N       MeS         N                                         EtO N EtS N                                                                   n-PrO N n-PrS N                                                               H.sub.2 C═CHCH.sub.2 O N H.sub.2 C═CHCH.sub.2 S N                     HC.tbd.CCH.sub.2 O N HC.tbd.CCH.sub.2 S N                                     CF.sub.3 O N CF.sub.3 S N                                                     (c-Pr)O N (c-Pr)S N                                                           MeO CH MeS CH                                                                 EtO CH EtS CH                                                                 n-PrO CH n-PrS CH                                                             H.sub.2 C═CHCH.sub.2 O CH H.sub.2 C═CHCH.sub.2 S CH                   HC.tbd.CCH.sub.2 O CH HC.tbd.CCH.sub.2 S CH                                   CF.sub.3 O CH CF.sub.3 S CH                                                   (c-Pr)O CH (c-Pr)S CH                                                       ______________________________________                                    

                                      TABLE 18                                    __________________________________________________________________________    Compounds of Formula I defined as:                                            __________________________________________________________________________      #STR105##                                                                      -                                                                          R.sup.2 = Me, W = O                                                           X       A X       A X       A X       A                                       __________________________________________________________________________        MeS O MeO S MeS S                                                           EtO O EtS O EtO S EtS S                                                       n-PrO O n-PrS O n-PrO S n-PrS S                                               H.sub.2 C═CHCH.sub.2 O O H.sub.2 C═CHCH.sub.2 S O H.sub.2                                                 C═CHCH.sub.2 O S H.sub.2                                                  C═CHCH.sub.2 S S                      HC.tbd.CCH.sub.2 O O HC.tbd.-CCH.sub.2 S O HC.tbd.CCH.sub.2 O S                                                   HC.tbd.CCH.sub.2 S S                      CF.sub.3 O O CF.sub.3 S O CF.sub.3 O S CF.sub.3 S S                           (c-Pr)O O (c-Pr)S O (c-Pr)O S (c-Pr)S S                                     __________________________________________________________________________    R.sup.2 = Et, W = O                                                           X       A X       A X       A X       A                                       __________________________________________________________________________      MeO O MeS O MeO S MeS S                                                       EtO O EtS O EtO S EtS S                                                       n-PrO O n-PrS O n-PrO S n-PrS S                                               H.sub.2 C═CHCH.sub.2 O O H.sub.2 C═CHCH.sub.2 S O H.sub.2                                                 C═CHCH.sub.2 O S H.sub.2                                                  C═CHCH.sub.2 S S                      HC.tbd.CCH.sub.2 O O HC.tbd.CCH.sub.2 S O HC.tbd.CCH.sub.2 O S HC.tbd.CC                                          H.sub.2 S S                               CF.sub.3 O O CF.sub.3 S O CF.sub.3 O S CF.sub.3 S S                           (c-Pr)O O (c-Pr)S O (c-Pr)O S (c-Pr)S S                                     __________________________________________________________________________    R.sup.2 = Me, W = S                                                           X       A X       A X       A X       A                                       __________________________________________________________________________      MeO O MeS O MeO S MeS S                                                       EtO O EtS O EtO S EtS S                                                       n-PrO O n-PrS O n-PrO S n-PrS S                                               H.sub.2 C═CHCH.sub.2 O O H.sub.2 C═CHCH.sub.2 S O H.sub.2                                                 C═CHCH.sub.2 O S H.sub.2                                                  C═CHCH.sub.2 S S                      HC.tbd.CCH.sub.2 O O HC.tbd.CCH.sub.2 S O HC.tbd.CCH.sub.2 O S HC.tbd.CC                                          H.sub.2 S S                               CF.sub.3 O O CF.sub.3 S O CF.sub.3 O S CF.sub.3 S S                           (c-Pr)O O (c-Pr)S O (c-Pr)O S (c-Pr)S S                                     __________________________________________________________________________    R.sup.2 = Et, W = S                                                           X       A X       A X       A X       A                                       __________________________________________________________________________      MeO O MeS O MeO S MeS S                                                       EtO O EtS O EtO S EtS S                                                       n-PrO O n-PrS O n-PrO S n-PrS S                                               H.sub.2 C═CHCH.sub.2 O O H.sub.2 C═CHCH.sub.2 S O H.sub.2                                                 C═CHCH.sub.2 O S H.sub.2                                                  C═CHCH.sub.2 S S                      HC.tbd.CCH.sub.2 O O HC.tbd.CCH.sub.2 S O HC.tbd.CCH.sub.2 O S HC.tbd.C-                                          CH.sub.2 S S                              CF.sub.3 O O CF.sub.3 S O CF.sub.3 CF.sub.3 O S CF.sub.3 S S                  (c-Pr)O O (c-Pr)S O (c-Pr)O S (c-Pr)S S                                     __________________________________________________________________________

                                      TABLE 19                                    __________________________________________________________________________    Compounds of Formula I defined as:                                              #STR106##                                                                      -                                                                          R.sup.9 R.sup.9 R.sup.9     R.sup.9                                           __________________________________________________________________________    2-Br--Ph                                                                              2-Me--Ph                                                                              2-Et--Ph    4-EtO-2-pyrimidinyl                                 2-CN--Ph 2-F--Ph 2-Cl--Ph 4,6-diMeO-2-pyrimidinyl                             2,4-diCl--Ph 2-Me-4-Cl--Ph 6-CF.sub.3 -2-pyridinyl 4,6-diMe-2-pyrimidiny                                l                                                   2-CF.sub.3 --Ph 3,5-diCl--Ph 2-pyrimidinyl 6-CF.sub.3 -4-pyrimidinyl                                     2-I--Ph 3,5-diCF.sub.3 --Ph 4-pyrimidinyl                                    4-CF.sub.3 -2-pyridinyl                             4-NO.sub.2 --Ph 2-MeO--Ph 4-MeO-2-pyrimidinyl 4-CF.sub.3 -2-pyrimidinyl       4-CF.sub.3 O--Ph 2,6-diMeO--Ph 4-Me-2-pyrimidinyl 5-CF.sub.3 -3-pyridiny                                l                                                   4-Me--Ph 3-CF.sub.3 O--Ph 6-MeO-4-pyrimidinyl 3-MeO-2-pyridinyl                                          4-Cl--Ph 4-Br--Ph 5-Me-2-furanyl 5-CN-2-pyrid                                inyl                                                3-Me--Ph 3-Et--Ph 2,5-diMe-3-thienyl 6-Me-2-pyridinyl                         3-CF.sub.3 --Ph 4-MeO--Ph 3-OCF.sub.2 H--Ph 3,5-diBr--Ph                      3-Cl-2-Me--Ph 4-t-Bu--Ph 4-OCF.sub.2 H--Ph 4-t-Bu-2-pyridinyl                 3-t-Bu--Ph 4-CN--Ph 3-Me.sub.3 Si--Ph 4-Me.sub.3 Si-2-pyridinyl                                          3-F--Ph 4-NO.sub.2 --Ph 4-Me.sub.3 Si--Ph                                    4-Me.sub.3 Ge-2-pyridinyl                           4-CF.sub.3 --Ph 3,4-diMe--Ph 3-Me.sub.3 Ge--Ph 4,6-diCF.sub.3 -2-pyrimid                                inyl                                                3,4-diCl--Ph 3,5-diMe--Ph 4-Me.sub.3 Ge--Ph 5-CF.sub.3 -2-furanyl                                        3,4-diCF.sub.3 --Ph 4-F-3-CF.sub.3 --Ph                                      3-EtO--Ph 5-CF.sub.3 -2-thienyl                     4-F--Ph 5-F-3-CF.sub.3 --Ph Ph (2-CN--Ph)CH.sub.2                             3,4-diF--Ph 3-Br-4-MeO--Ph 4,5-diBr-2-thienyl (2-CF.sub.3 --Ph)CH.sub.2       3-Cl-4-Me--Ph 5-F-2-thienyl 4,5-diCl-2-thienyl (3-CF.sub.3 --Ph)CH.sub.2      3,5-diF--Ph 5-Br-2-thienyl 4,5-diF-2-thienyl (4-CF.sub.3 --Ph)CH.sub.2                                   3-F-4-Cl--Ph 5-Cl-2-thienyl 2-CF.sub.3                                       CH.sub.2 O-5-pyridinyl (3,5-diCF.sub.3                                        --Ph)CH.sub.2                                       3-MeO--Ph 2,5-diF-3-thienyl (4-Cl--Ph)CH.sub.2 (2-CF.sub.3 O--Ph)CH.sub.                                2                                                   3-Cl--Ph 2,5-diCl-3-thienyl (3-Cl--Ph)CH.sub.2 (3-CF.sub.3 O--Ph)CH.sub.                                2                                                   t-Bu 2,5-diBr-3-thienyl (2-Cl--Ph)CH.sub.2 (4-CF.sub.3 O--Ph)CH.sub.2                                    3-Br--Ph 2-I--Ph (2-Br--Ph)CH.sub.2 2,6-diCl-                                4-pyridinyl                                         4-Ph--Ph 3-I--Ph (3-Br--Ph)CH.sub.2 (2,6-diCl--Ph)CH.sub.2                    4-Br-3-Me--Ph 2-Br-5-pyridinyl (4-Br--Ph)CH.sub.2                           __________________________________________________________________________

                                      TABLE 20                                    __________________________________________________________________________    Compounds of Formula I defined as:                                              #STR107##                                                                      -                                                                          R.sup.9 R.sup.9 R.sup.9     R.sup.9                                           __________________________________________________________________________    2-Br--Ph                                                                              2-Me--Ph                                                                              2-Et--Ph    4-EtO-2-pyrimidinyl                                 2-CN--Ph 2-F--Ph 2-Cl--Ph 4,6-diMeO-2-pyrimidinyl                             2,4-diCl--Ph 2-Me-4-Cl--Ph 6-CF.sub.3 -2-pyridinyl 4,6-diMe-2-pyrimidiny                                l                                                   2-CF.sub.3 --Ph 3,5-diCl--Ph 2-pyrimidinyl 6-CF.sub.3 -4-pyrimidinyl                                     2-I--Ph 3,5-diCF.sub.3 --Ph 4-pyrimidinyl                                    4-CF.sub.3 -2-pyridinyl                             4-NO.sub.2 --Ph 2-MeO--Ph 4-MeO-2-pyrimidinyl 4-CF.sub.3 -2-pyrimidinyl       4-CF.sub.3 O--Ph 2,6-diMeO--Ph 4-Me-2-pyrimidinyl 5-CF.sub.3 -3-pyridiny                                l                                                   4-Me--Ph 3-CF.sub.3 O--Ph 6-MeO-4-pyrimidinyl 3-MeO-2-pyridinyl                                          4-Cl--Ph 4-Br--Ph 5-Me-2-furanyl 5-CN-2-pyrid                                inyl                                                3-Me--Ph 3-Et--Ph 2,5-diMe-3-thienyl 6-Me-2-pyridinyl                         3-CF.sub.3 --Ph 4-MeO--Ph 3-OCF.sub.2 H--Ph 3,5-diBr--Ph                      3-Cl-2-Me--Ph 4-t-Bu--Ph 4-OCF.sub.2 H--Ph 4-t-Bu-2-pyridinyl                 3-t-Bu--Ph 4-CN--Ph 3-Me.sub.3 Si--Ph 4-Me.sub.3 Si-2-pyridinyl                                          3-F--Ph 4-NO.sub.2 --Ph 4-Me.sub.3 Si--Ph                                    4-Me.sub.3 Ge-2-pyridinyl                           4-CF.sub.3 --Ph 3,4-diMe--Ph 3-Me.sub.3 Ge--Ph 4,6-diCF.sub.3 -2-pyrimid                                inyl                                                3,4-diCl--Ph 3,5-diMe--Ph 4-Me.sub.3 Ge--Ph 5-CF.sub.3 -2-furanyl                                        3,4-diCF.sub.3 --Ph 4-F-3-CF.sub.3 --Ph                                      3-EtO--Ph 5-CF.sub.3 -2-thienyl                     4-F--Ph 5-F-3-CF.sub.3 --Ph Ph (2-CN--Ph)CH.sub.2                             3,4-diF--Ph 3-Br-4-MeO--Ph 4,5-diBr-2-thienyl (2-CF.sub.3 --Ph)CH.sub.2       3-Cl-4-Me--Ph 5-F-2-thienyl 4,5-diCl-2-thienyl (3-CF.sub.3 --Ph)CH.sub.2      3,5-diF--Ph 5-Br-2-thienyl 4,S-diF-2-thienyl (4-CF.sub.3 --Ph)CH.sub.2                                   3-F-4-Cl--Ph 5-Cl-2-thienyl 2-CF.sub.3                                       CH.sub.2 O-5-pyridinyl (3,5-diCF.sub.3                                        --Ph)CH.sub.2                                       3-MeO--Ph 2,5-diF-3-thienyl (4-Cl--Ph)CH.sub.2 (2-CF.sub.3 O--Ph)CH.sub.                                2                                                   3-Cl--Ph 2,5-diCl-3-thienyl (3-Cl--Ph)CH.sub.2 (3-CF.sub.3 O--Ph)CH.sub.                                2                                                   t-Bu 2,5-diBr-3-thienyl (2-Cl--Ph)CH.sub.2 (4-CF.sub.3 O--Ph)CH.sub.2                                    3-Br--Ph 2-I--Ph (2-Br--Ph)CH.sub.2 2,6-diCl-                                4-pyridinyl                                         4-Ph--Ph 3-I--Ph (3-Br--Ph)CH.sub.2 (2,6-diCl--Ph)CH.sub.2                    4-Br-3-Me--Ph 2-Br-5-pyridinyl (4-Br--Ph)CH.sub.2                           __________________________________________________________________________

                                      TABLE 21                                    __________________________________________________________________________    Compounds of Formula I defined as:                                              #STR108##                                                                      -                                                                          R.sup.9 R.sup.9 R.sup.9     R.sup.9                                           __________________________________________________________________________    2-Br--Ph                                                                              2-Me--Ph                                                                              2-Et--Ph    4-EtO-2-pyrimidinyl                                 2-CN--Ph 2-F--Ph 2-Cl--Ph 4,6-diMeO-2-pyrimidinyl                             2,4-diCl--Ph 2-Me-4-Cl--Ph 6-CF.sub.3 -2-pyridinyl 4,6-diMe-2-pyrimidiny                                l                                                   2-CF.sub.3 --Ph 3,5-diCl--Ph 2-pyrimidinyl 6-CF.sub.3 -4-pyrimidinyl                                     2-I--Ph 3,5-diCF.sub.3 --Ph 4-pyrimidinyl                                    4-CF.sub.3 -2-pyridinyl                             4-NO.sub.2 --Ph 2-MeO--Ph 4-MeO-2-pyrimidinyl 4-CF.sub.3 -2-pyrimidinyl       4-CF.sub.3 O--Ph 2,6-diMeO--Ph 4-Me-2-pyrimidinyl 5-CF.sub.3 -3-pyridiny                                l                                                   4-Me--Ph 3-CF.sub.3 O--Ph 6-MeO-4-pyrimidinyl 3-MeO-2-pyridinyl                                          4-Cl--Ph 4-Br--Ph 5-Me-2-furanyl 5-CN-2-pyrid                                inyl                                                3-Me--Ph 3-Et--Ph 2,5-diMe-3-thienyl 6-Me-2-pyridinyl                         3-CF.sub.3 --Ph 4-MeO--Ph 3-OCF.sub.2 H--Ph 3,5-diBr--Ph                      3-Cl-2-Me--Ph 4-t-Bu--Ph 4-OCF.sub.2 H--Ph 4-t-Bu-2-pyridinyl                 3-t-Bu--Ph 4-CN--Ph 3-Me.sub.3 Si--Ph 4-Me.sub.3 Si-2-pyridinyl                                          3-F--Ph 4-NO.sub.2 --Ph 4-Me.sub.3 Si--Ph                                    4-Me.sub.3 Ge-2-pyridinyl                           4-CF.sub.3 --Ph 3,4-diMe--Ph 3-Me.sub.3 Ge--Ph 4,6-diCF.sub.3 -2-pyrimid                                inyl                                                3,4-diCl--Ph 3,5-diMe--Ph 4-Me.sub.3 Ge--Ph 5-CF.sub.3 -2-furanyl                                        3,4-diCF.sub.3 --Ph 4-F-3-CF.sub.3 --Ph                                      3-EtO--Ph 5-CF.sub.3 -2-thienyl                     4-F--Ph 5-F-3-CF.sub.3 --Ph Ph (2-CN--Ph)CH.sub.2                             3,4-diF--Ph 3-Br-4-MeO--Ph 4,5-diBr-2-thienyl (2-CF.sub.3 --Ph)CH.sub.2       3-Cl-4-Me-Ph 5-F-2-thienyl 4,5-diCl-2-thienyl (3-CF.sub.3 --Ph)CH.sub.2       3,5-diF-Ph 5-Br-2-thienyl 4,5-diF-2-thienyl (4-CF.sub.3 --Ph)CH.sub.2                                    3-F-4-Cl--Ph 5-Cl-2-thienyl 2-CF.sub.3                                       CH.sub.2 O-5-pyridinyl (3,5-diCF.sub.3                                        --Ph)CH.sub.2                                       3-MeO--Ph 2,5-diF-3-thienyl (4-Cl--Ph)CH.sub.2 (2-CF.sub.3 O--Ph)CH.sub.                                2                                                   3-Cl--Ph 2,5-diCl-3-thienyl (3-Cl--Ph)CH.sub.2 (3-CF.sub.3 O--Ph)CH.sub.                                2                                                   t-Bu 2,5-diBr-3-thienyl (2-Cl--Ph)CH.sub.2 (4-CF.sub.3 O--Ph)CH.sub.2                                    3-Br--Ph 2-I--Ph (2-Br--Ph)CH.sub.2 2,6-diCl-                                4-pyridinyl                                         4-Ph--Ph 3-I--Ph (3-Br--Ph)CH.sub.2 (2,6-diCl--Ph)CH.sub.2                    4-Br-3-Me--Ph 2-Br-5-pyridinyl (4-Br--Ph)CH.sub.2                           __________________________________________________________________________

Formulation/Utility

Compounds of this invention will generally be used as a formulation orcomposition with an agriculturally suitable carrier comprising at leastone of a liquid diluent, a solid diluent or a surfactant. Theformulation or composition ingredients are selected to be consistentwith the physical properties of the active ingredient, mode ofapplication and environmental factors such as soil type, moisture andtemperature. Useful formulations include liquids such as solutions(including emulsifiable concentrates), suspensions, emulsions (includingmicroemulsions and/or suspoemulsions) and the like which optionally canbe thickened into gels. Useful formulations further include solids suchas dusts, powders, granules, pellets, tablets, films, and the like whichcan be water-dispersible ("wettable") or water-soluble. Activeingredient can be (micro)encapsulated and further formed into asuspension or solid formulation; alternatively the entire formulation ofactive ingredient can be encapsulated (or "overcoated"). Encapsulationcan control or delay release of the active ingredient. Sprayableformulations can be extended in suitable media and used at spray volumesfrom about one to several hundred liters per hectare. High-strengthcompositions are primarily used as intermediates for furtherformulation.

The formulations will typically contain effective amounts of activeingredient, diluent and surfactant within the following approximateranges which add up to 100 percent by weight.

    ______________________________________                                                      Weight Percent                                                                  Active                                                          Ingredient Diluent Surfactant                                               ______________________________________                                        Water-Dispersible and                                                                         5-90       0-94     1-15                                        Water-soluble Granules, Tablets                                               and Powders.                                                                  Suspensions, Emulsions, 5-50 40-95 0-15                                       Solutions (including                                                          Emulsifiable Concentrates)                                                    Dusts 1-25 70-99 0-5                                                          Granules and Pellets 0.01-99      5-99.99 0-15                                High Strength Compositions 90-99   0-10 0-2                                 ______________________________________                                    

Typical solid diluents are described in Watkins, et al., Handbook ofInsecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books,Caldwell, N.J. Typical liquid diluents are described in Marsden,Solvents Guide, 2nd Ed., Interscience, New York, 1950. McCutcheon 'sDetergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, N.J.,as well as Sisely and Wood, Encyclopedia of Surface Active Agents,Chemical Publ. Co., Inc., New York, 1964, list surfactants andrecommended uses. All formulations can contain minor amounts ofadditives to reduce foam, caking, corrosion, microbiological growth andthe like, or thickeners to increase viscosity.

Surfactants include, for example, polyethoxylated alcohols,polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acidesters, dialkyl sulfosuccinates, alkyl sulfates, alkylbenzenesulfonates, organosilicones, N,N-dialkyltaurates, lignin sulfonates,naphthalene sulfonate formaldehyde condensates, polycarboxylates, andpolyoxyethylene/polyoxypropylene block copolymers. Solid diluentsinclude, for example, clays such as bentonite, montmorillonite,attapulgite and kaolin, starch, sugar, silica, talc, diatomaceous earth,urea, calcium carbonate, sodium carbonate and bicarbonate, and sodiumsulfate. Liquid diluents include, for example, water,N,N-dimethylformamide, dimethyl sulfoxide, N-alkylpyrrolidone, ethyleneglycol, polypropylene glycol, paraffms, alkylbenzenes,alkylnaphthalenes, oils of olive, castor, linseed, tung, sesame, corn,peanut, cotton-seed, soybean, rape-seed and coconut, fatty acid esters,ketones such as cyclohexanone, 2-heptanone, isophorone and4-hydroxy-4-methyl-2-pentanone, and alcohols such as methanol,cyclohexanol, decanol and tetrahydrofurfuryl alcohol.

Solutions, including emulsifiable concentrates, can be prepared bysimply mixing the ingredients. Dusts and powders can be prepared byblending and, usually, grinding as in a hammer mill or fluid-energymill. Suspensions are usually prepared by wet-milling; see, for example,U.S. Pat. No. 3,060,084. Granules and pellets can be prepared byspraying the active material upon preformed granular carriers or byagglomeration techniques. See Browning, "Agglomeration", ChemicalEngineering, Dec. 4, 1967, pp 147-48, Perry's Chemical Engineer'sHandbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 andfollowing, and WO 91/13546. Pellets can be prepared as described in U.S.Pat. No. 4,172,714. Water-dispersible and water-soluble granules can beprepared as taught in U.S. Pat. No. 4,144,050, U.S. Pat. No. 3,920,442and DE 3,246,493. Tablets can be prepared as taught in U.S. Pat. No.5,180,587, U.S. Pat. No. 5,232,701 and U.S. Pat. No. 5,208,030. Filmscan be prepared as taught in GB 2,095,558 and U.S. Pat. No. 3,299,566.

For further information regarding the art of formulation, see U.S. Pat.No. 3,235,361, Col. 6, line 16 through Col. 7, line 19 and Examples10-41; U.S. Pat. No. 3,309,192, Col. 5, line 43 through Col. 7, line 62and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166,167 and 169-182; U.S. Pat. No. 2,891,855, Col. 3, line 66 through Col.5, line 17 and Examples 1-4; Klingman, Weed Control as a Science, JohnWiley and Sons, Inc., New York, 1961, pp 81-96; and Hance et al., WeedControl Handbook, 8th Ed., Blackwell Scientific Publications, Oxford,1989.

In the following Examples, all percentages are by weight and allformulations are prepared in conventional ways. Compound numbers referto compounds in Index Tables A-G.

Example A

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        Compound 17           65.0%                                                     dodecylphenol polyethylene glycol ether 2.0%                                  sodium ligninsulfonate 4.0%                                                   sodium silicoaluminate 6.0%                                                   montmorillonite (calcined) 23.0%.                                           ______________________________________                                    

Example B

    ______________________________________                                        Granule                                                                       ______________________________________                                        Compound 17            10.0%                                                    attapulgite granules (low volatile matter, 90.0%.                             0.71/0.30 mm; U.S.S. No. 25-50 sieves)                                      ______________________________________                                    

Example C

    ______________________________________                                        Extruded Pellet                                                               ______________________________________                                        Compound 17          25.0%                                                      anhydrous sodium sulfate 10.0%                                                crude calcium ligninsulfonate 5.0%                                            sodium alkylnaphthalenesulfonate 1.0%                                         calcium/magnesium bentonite 59.0%.                                          ______________________________________                                    

Example D

    ______________________________________                                        Emulsifiable Concentrate                                                      ______________________________________                                        Compound 17         20.0%                                                       blend of oil soluble sulfonates 10.0%                                         and polyoxyethylene ethers                                                    isophorone 70.0%.                                                           ______________________________________                                    

The compounds of this invention are useful as plant disease controlagents. The present invention therefore further comprises a method forcontrolling plant diseases caused by fungal plant pathogens comprisingapplying to the plant or portion thereof to be protected, or to theplant seed or seedling to be protected, an effective amount of acompound of the invention or a fungicidal composition containing saidcompound. The compounds and compositions of this invention providecontrol of diseases caused by a broad spectrum of fungal plant pathogensin the Basidiomycete, Ascomycete, Oomycete and Deuteromycete classes.They are effective in controlling a broad spectrum of plant diseases,particularly foliar pathogens of ornamental, vegetable, field, cereal,and fruit crops. These pathogens include Plasmopara viticola,Phytophthora infestans, Peronospora tabacina, Pseudoperonosporacubensis, Pythium aphanidermatum, Alternaria brassicae, Septorianodorum, Septoria tritici, Cercosporidium personatum, Cercosporaarachidicola, Pseudocercosporella herpotrichoides, Cercospora beticola,Botrytis cinerea, Moniliniafructicola, Pyricularia oryzae, Podosphaeraleucotricha, Venturia inaequalis, Erysiphe graminis, Uncinula necatur,Puccinia recondita, Puccinia graminis, Hemileia vastatrix, Pucciniastriiformis, Puccinia arachidis, Rhizoctonia solani,Sphaerothecafuliginea, Fusarium oxysporum, Verticillium dahliae, Pythiumaphanidermatum, Phytophthora megasperma, Sclerotinia scierotiorum,Sclerotium rolfsii, Erysiphe polygoni, Pyrenophora teres, Gaeumannomycesgraminis, Rynchosporium secalis, Fusarium roseum, Bremia lactucae andother generea and species closely related to these pathogens.

Compounds of this invention can also be mixed with one or more otherinsecticides, fungicides, nematocides, bactericides, acaricides, growthregulators, chemosterilants, semiochemicals, repellents, attractants,pheromones, feeding stimulants or other biologically active compounds toform a multi-component pesticide giving an even broader spectrum ofagricultural protection. Examples of such agricultural protectants withwhich compounds of this invention can be formulated are: insecticidessuch as abamnectin, acephate, azinphos-methyl, bifenthrin, buprofezin,carbofuran, chlorpyrifos, chlorpyrifos-methyl, cyfluthrin,beta-cyfluthrin, deltamnethrin, diafenthiuron, diazinon, diflubenzuron,dimethoate, esfenvalerate, fenpropathrin, fenvalerate, fipronil,flucythrinate, tau-fluvalinate, fonophos, imidacloprid, isofenphos,malathion, metaldehyde, methamidophos, methidathion, methomyl,methoprene, methoxychlor, monocrotophos, oxamyl, parathion,parathion-methyl, permethrin, phorate, phosalone, phosmet,phospharnidon, pirimicarb, profenofos, rotenone, sulprofos,tebufenozide, tefluthrin, terbufos, tetrachlorvinphos, thiodicarb,tralomethrin, trichlorfon and triflumuron; fungicides such asazoxystrobin (ICIA5504), benomyl, blasticidin-S, Bordeaux mixture(tribasic copper sulfate), bromuconazole, captafol, captan, carbendazim,chloroneb, chlorothalonil, copper oxychloride, copper salts, cymoxanil,cyproconazole, cyprodinil (CGA 219417), diclomezine, dicloran,difenoconazole, dimethomorph, diniconazole, diniconazole-M, dodine,edifenphos, epoxyconazole (BAS 480F), fenarimol, fenbuconazole,fenpiclonil, fenpropidin, fenpropimorph, fluquinconazole, flusilazole,flutolanil, flutriafol, folpet, fosetyl-aluminum, furalaxyl,hexaconazole, ipconazole, iprobenfos, iprodione, isoprothiolane,kasugamycin, kresoxim-methyl (BAS 490F), mancozeb, maneb, mepronil,metalaxyl, metconazole, myclobutanil, neo-asozin (ferricmethanearsonate), oxadixyl, penconazole, pencycuron, probenazole,prochloraz, propiconazole, pyrifenox, pyroquilon, sulfur, tebuconazole,tetraconazole, thiabendazole, thiophanate-methyl, thiram, triadimefon,triadimenol, tricyclazole, triticonazole, uniconazole, validamycin andvinclozolin; nematocides such as aldoxycarb and fenamiphos; bactericidessuch as streptomycin; acaricides such as amitraz, chinomethionat,chlorobenzilate, cyhexatin, dicofol, dienochlor, fenazaquin, fenbutatinoxide, fenpropathrin, fenpyroximate, hexythiazox, propargite, pyridabenand tebufenpyrad; and biological agents such as Bacillus thuringiensis,Bacillus thuringiensis delta endotoxin, baculovirus, andentomopathogenic bacteria, virus and fungi.

In certain instances, combinations with other fungicides having asimilar spectrum of control but a different mode of action will beparticularly advantageous for resistance management.

Preferred for better control of plant diseases caused by fungal plantpathogens (e.g., lower use rate or broader spectrum of plant pathogenscontrolled) or resistance management are mixtures of a compound of thisinvention with a fungicide selected from the group cyproconazole,cyprodinil (CGA 219417), epoxyconazole (BAS 480F), fenpropidin,fenpropimorph, flusilazole and tebuconazole. Specifically preferredmixtures (compound numbers refer to compounds in Index Tables A-G) areselected from the group: compound 1 and cyproconazole; compound 1 andcyprodinil (CGA 219417); compound 1 and epoxyconazole (BAS 480F);compound 1 and fenpropidin; compound 1 and fenpropimorph; compound 1 andflusilazole; compound 1 and tebuconazole; compound 2 and cyproconazole;compound 2 and cyprodinil (CGA 219417); compound 2 and epoxyconazole(BAS 480F); compound 2 and fenpropidin; compound 2 and fenpropimorph;compound 2 and flusilazole; compound 2 and tebuconazole; compound 4 andcyproconazole; compound 4 and cyprodinil (CGA 219417); compound 4 andepoxyconazole (BAS 480F); compound 4 and fenpropidin; compound 4 andfenpropimorph; compound 4 and flusilazole; compound 4 and tebuconazole;compound 6 and cyproconazole; compound 6 and cyprodinil (CGA 219417);compound 6 and epoxyconazole (BAS 480F); compound 6 and fenpropidin;compound 6 and fenpropimorph; compound 6 and flusilazole; compound 6 andtebuconazole; compound 15 and cyproconazole; compound 15 and cyprodinil(CGA 219417); compound 15 and epoxyconazole (BAS 480F); compound 15 andfenpropidin; compound 15 and fenpropimorph; compound 15 and flusilazole;compound 15 and tebuconazole; compound 17 and cyproconazole; compound 17and cyprodinil (CGA 219417); compound 17 and epoxyconazole (BAS 480F);compound 17 and fenpropidin; compound 17 and fenpropimorph; compound 17and flusilazole; and compound 15 and tebuconazole.

Plant disease control is ordinarily accomplished by applying aneffective amount of a compound of this invention either pre- orpost-infection, to the portion of the plant to be protected such as theroots, stems, foliage, fruit, seeds, tubers or bulbs, or to the media(soil or sand) in which the plants to be protected are growing. Thecompounds can also be applied to the seed to protect the seed andseedling.

Rates of application for these compounds can be influenced by manyfactors of the environment and should be determined under actual useconditions. Foliage can normally be protected when treated at a rate offrom less than 1 g/ha to 5,000 g/ha of active ingredient. Seed andseedlings can normally be protected when seed is treated at a rate offrom 0.1 to 10 g per kilogram of seed.

The following TESTS demonstrate the control efficacy of compounds ofthis invention on specific pathogens. The pathogen control protectionafforded by the compounds is not limited, however, to these species. SeeIndex Tables A-G for compound descriptions. The following abbreviationsare used in the Index Tables which follow: Ph=phenyl and PhO=phenoxy.The abbreviation "Ex." stands for "Example" and is followed by a numberindicating in which example the compound is prepared.

                                      INDEX TABLE A                               __________________________________________________________________________      #STR109##                                                                      -                                                                          Cmpd No.                                                                           X   Y            Z                m.p. (° C.)                     __________________________________________________________________________     1 Ex. 2                                                                           CH.sub.3 O                                                                        --CH.sub.2 O--N═C(CH.sub.3)--                                                          3-(CH.sub.3).sub.3 Si--Ph                                                                      oil/gum*                                  2 Ex. 3 CH.sub.3 O --CH.sub.2 O-- 2,5-diCH.sub.3 --Ph 151-153                 3 Ex. 1 CH.sub.3 O direct bond CH.sub.2 Br 117-118                            4 CH.sub.3 O --CH.sub.2 O--N═C(CH.sub.3)-- 3-CF.sub.3 --Ph 91-93                                                5.sup.a Ex. 4 CH.sub.3 O                                                    --CH═C(Cl)-C(═O)--O-- t-Bu                                            105-115                                   6.sup.b Ex. 4 CH.sub.3 O --CH═C(Cl)-C(═O)--O-- t-Bu 104                                                     7 CH.sub.3 O --CH.sub.2 O--N═                                           C(CH.sub.3)-- 4-CF.sub.3 -pyridin-2                                           -yl   101-103.5                           8 CH.sub.3 O direct bond 3-(3-CF.sub.3 --Ph)-1,2,4-oxadiazol-5-yl 158                                               9 CH.sub.3 O --CH.sub.2 O--N═                                           C(CH.sub.3)-- 3,4-diCl--Ph 132-134       10 CH.sub.3 O --CH.sub.2 O--N═C(NH.sub.2)-- 3-CF.sub.3 --Ph 123-124       11 CH.sub.3 O --CH.sub.2 O--N═C(CH.sub.3)-- 3,5-diBr--Ph 150.5-151        12 CH.sub.3 O --CH.sub.2 O--N═C(CH.sub.3)-- 3,5-diCl--Ph 159-160                                                13 CH.sub.3 O --CH.sub.2 O--N═                                           C(CH.sub.3)-- 2-naphthalenyl                                                  124-125                                  14.sup.c CH.sub.3 O --CH.sub.2 O--N═C(CH.sub.2 CH.sub.3)-- 3-CF.sub.                                           3 --Ph oil*                              15 CH.sub.3 O --CH.sub.2 O-- 3-(4-Cl--Ph)-1,2,4-thiadiazol-5-yl 184-185       16 CH.sub.3 O --CH.sub.2 O-- 3-(3,5-diCl--Ph)-1,2,4-thiadiazol-5-yl                                                185-186                                  17 Ex. 10 CH.sub.3 O --CH.sub.2 O-- 3-(4-CF.sub.3 --Ph)-1,2,4-thiadiazol                                           -5-yl 138-139                          __________________________________________________________________________     *See Index Table G for .sup.1 H NMR data.                                     .sup.a Compound isolated in a 7:3 ratio of Z and E isomers, respectively.     .sup.b Compound isolated in a 5:1 ratio of Z and E isomers, respectively.     .sup.c Compound contains 28% by weight of                                     2,4dihydro-5-methoxy-2-methyl-4-[5-methyl-2-[[[[1-[3-(trifluoromethyl)phe    yl]ethylene]amino]oxy]methyl]-3-thienyl]-3H-1,2,4-triazol-3-one which is       also a compound of this invention.                                       

                                      INDEX TABLE B                               __________________________________________________________________________      #STR110##                                                                      -                                                                          Cmpd No.                                                                           X   Y            Z                m.p. (° C.)                     __________________________________________________________________________    18   CH.sub.3 O                                                                        direct bond  CH.sub.2 Br      132-133                                  19 CH.sub.3 O --CH.sub.2 O--N═C(CH.sub.3)-- 3,4-diCl--Ph 143-144                                                20 CH.sub.3 O --CH.sub.2 O--N═                                           C(CH.sub.3)-- 3-(CH.sub.3).sub.3                                              Si--Ph oil*                              21 CH.sub.3 O --CH.sub.2 O--N═C(CH.sub.3)-- 4-CF.sub.3 -pyridin-2-yl                                            123-125                                 22 CH.sub.3 O --CH.sub.2 O--N═C(CH.sub.3)-- 3-CF.sub.3 --Ph             __________________________________________________________________________                                           87-89                                   *See Index Table G for .sup.1 H NMR data.                                

                                      INDEX TABLE C                               __________________________________________________________________________      #STR111##                                                                      -                                                                          Cmpd No.                                                                           X   Y            Z                m.p. (° C.)                     __________________________________________________________________________    23   Cl  direct bond  CH.sub.3          99-101                                  24 CH.sub.3 O direct bond CH.sub.3 123-125                                    25 CH.sub.3 O --CH.sub.2 O--N═C(CH.sub.3)-- 3-CF.sub.3 --Ph oil*                                                26 CH.sub.3 O --CH.sub.2 O--N═                                           C(CH.sub.3)-- 4-CF.sub.3 -pyridin-2                                           -yl 106-107                              27 CH.sub.3 O --CH.sub.2 O--N═C(CH.sub.3)-- 3,4-diCl--Ph 102-104                                                28 CH.sub.3 O --CH.sub.2 O--N═                                           C(CH.sub.3)-- 3-(CH.sub.3).sub.3                                              Si--Ph 135-137                           29 CH.sub.3 O --CH.sub.2 O--N═C(CH.sub.3)-- 3,5-diCl--Ph 135-137                                                30 CH.sub.3 O --CH.sub.2 O--N═                                           C(CH.sub.3)-- 3,5-diBr--Ph 145-147       31 CH.sub.3 O --CH.sub.2 O--N═C(NH.sub.2)-- 3-CF.sub.3 --Ph 147-148       32 CH.sub.3 O --CH.sub.2 S-- 5-CF.sub.3 -4H-1,2,4-triazol-3-yl 178-179                                              33 CH.sub.3 O direct bond                                                    3-(3-CF.sub.3 --Ph)-1,2,4-oxadiazol                                           -5-yl 165-166                            34 CH.sub.3 O --CH.sub.2 -- 3-CF.sub.3 -1H-pyrazol-1-yl  99-100                                                     35 CH.sub.3 O --CH.sub.2 O--                                                 2-Cl-5-CF.sub.3 --Ph 106-108                                                   36 CH.sub.3 O --CH.sub.2 O--                                                 2,5-diCH.sub.3 --Ph 91-93                37 CH.sub.3 O --CH.sub.2 O--N═C(CH.sub.3)-- 2-naphthalenyl semisolid                                           *                                        38 Ex. 9 CH.sub.3 O --O-- 3-PhO--Ph 113-114                                   39 Ex. 8 Cl --O-- 3-PhO--Ph 72-75                                           __________________________________________________________________________     *See Index Table G for .sup.1 H NMR data.                                

                                      INDEX TABLE D                               __________________________________________________________________________      #STR112##                                                                      -                                                                          Cmpd No.                                                                           X   Y            Z                m.p. (° C.)                     __________________________________________________________________________    40   CH.sub.3 O                                                                        direct bond  3-(3-CF.sub.3 --Ph)-1,2,4-oxadiazol-5-yl                                                       149-150                                  41 Ex. 5 CH.sub.3 O direct bond CH.sub.2 Br 147-149                           42 CH.sub.3 O --CH.sub.2 O--N═C(CH.sub.3)-- 2-naphthalenyl 134-136                                              43 CH.sub.3 O --CH.sub.2 O--N═                                           C(CH.sub.3)-- 3,4-diCl--Ph 118-119       44 CH.sub.3 O --CH.sub.2 O--N═C(CH.sub.3)-- 4-CF.sub.3 -pyridin-2-yl                                            125-127                                 45 CH.sub.3 O --CH.sub.2 O--N═C(CH.sub.3)-- 3,5-diCl--Ph 148.5-150.5      46 Ex. 6 CH.sub.3 O --CH.sub.2 O--N═C(CH.sub.3)-- 3-(CH.sub.3).sub.3                                            Si--Ph oil*                             47 CH.sub.3 O --CH.sub.2 O--N═C(NH.sub.2)-- 3-CF.sub.3 --Ph                                                    semisolid*                               48 CH.sub.3 O --CH.sub.2 O--N═C(CH.sub.3)-- 3-CF.sub.3 --Ph 81-83                                               49 CH.sub.3 O --CH.sub.2 O--N═                                           C(CH.sub.3)-- 3,5-diBr--Ph                                                    126.5-127.5                            __________________________________________________________________________     *See Index Table G for .sup.1 H NMR data.                                

                                      INDEX TABLE E                               __________________________________________________________________________      #STR113##                                                                      -                                                                          Cmpd No.                                                                           X   Y            Z                m.p. (° C.)                     __________________________________________________________________________    50 Ex. 7                                                                           CH.sub.3 O                                                                        --O--        3-(4-CF.sub.3 --Ph)-1,2,4-thiadiazol-5-yl                                                      216-217                                  51 CH.sub.3 O --O-- 3-(3,5-diCl--Ph)-1,2,4-thiadiazol-5-yl 222-223                                                  52 CH.sub.3 O --O-- 3-(4-Cl--Ph)-1                                           ,2,4-thiadiazol-5-yl 226-227           __________________________________________________________________________

                                      INDEX TABLE F                               __________________________________________________________________________      #STR114##                                                                      -                                                                          Cmpd No.                                                                           X   Y            Z                m.p. (° C.)                     __________________________________________________________________________      53 CH.sub.3 O --CH.sub.2 O--N═C(CH.sub.3)-- 3-CF.sub.3 --Ph             __________________________________________________________________________                                           153-155                            

                                      INDEX TABLE G                               __________________________________________________________________________    Cmpd No.                                                                            .sup.1 H NMR Data (CDCl.sub.3 solution unless indicated otherwise).s          up.a                                                                    __________________________________________________________________________     1    δ 7.76 (s, 1H), 7.60 (m, 1H), 7.54 (m, 1H), 7.36 (d, 1H),               7.32 (d, 1H), 6.94                                                         (d, 1H), 5.29 (s, 2H), 3.89 (s, 3H), 3.41 (s, 3H), 2.21 (s, 3H) 0.28             (s, 9H).                                                                  14 major component: δ 7.33 (d, 1H), 6.95 (d, 1H), 5.31 (d, 2H),             3.904 (s, 3H),                                                             3.42 (s, 3H), 2.74 (q, 2H), 1.11 (t, 3H) plus peaks overlapping with             minor                                                                      component at 7.88 (d), 7.79 (m), 7.61 (d), 7.49 (t);                          minor component: δ 6.62 (s, 1H), 5.22 (d, 2H), 3.899 (s, 3H),              3.41 (s, 3H),                                                              2.45 (s, 3H), 2.22 (d, 3H) plus peaks overlapping with major component           at                                                                         7.88 (d), 7.79 (m), 7.61 (d), 7.49 (t).                                      20 δ 7.67 (s, 1H), 7.52 (m, 3H), 7.40 (d, 1H), 7.33 (m, 2H), 7.26           (m, 1H), 5.35                                                              (br s, 2H), 3.77 (s, 3H), 3.44 (s, 3H), 2.20 (s, 3H), 0.27 (s, 9H).               25 δ 8.68 (m, 1H), 7.80 (s, 1H), 7.75 (d, 1H), 7.60 (m, 2H),           7.47-7.37 (m, 2H),                                                         5.47 (AB pattern, 2H), 3.82 (s, 3H), 3.35 (s, 3H), 2.16 (s, 3H).                  37 δ 8.69 (m, 1H), 7.94 (s, 1H), 7.85-7.73 (m, 4H), 7.61 (d,           1H), 7.59-7.45                                                             (m, 2H), 7.38 (dd, 1H), 5.50 (AB pattern, 2H), 3.78 (s, 3H); 3.35 (s,            3H),                                                                       2.25 (s, 3H).                                                                46 δ 7.70 (s, 1H), 7.54 (m, 4H), 7.34 (t, 1H), 5.11 (s, 2H), 3.86           (s, 3H),                                                                   3.32 (s, 3H), 2.14 (s, 3H), 0.28 (s, 9H).                                    47 δ 7.86 (s, 1H), 7.76 (d, 1H), 7.64 (d, 1H), 7.59 (d, 1H), 7.54           (d, 1H),                                                                   7.53-7.47 (m, 1H), 5.01 (br s, 2H), 4.96 (s, 2H), 3.89 (s, 3H), 3.33             (s, 3H).                                                                __________________________________________________________________________     .sup.a1 H NMR data are in ppm downfield from tetramethylsilane. Couplings     are designated by (s)singlet, (d)doublet, (t)triplet, (q)quartet,             (m)multiplet, (dd)doublet of doublets, (br s)broad singlet.              

BIOLOGICAL EXAMPLES OF THE INVENTION

The compounds were first dissolved in acetone in an amount equal to 3%of the final volume and then suspended at a concentration of 200 ppm inpurified water containing 250 ppm of the surfactant Trem® 014(polyhydric alcohol esters). The resulting test suspensions were thenused in the following tests. Spraying these 200 ppm test suspensions tothe point of run-off on the test plants is the equivalent of a rate of500 g/ha

Test A

The test suspension was sprayed to the point of run-off on wheatseedlings. The following way the seedlings were inoculated with a sporedust of Erysiphe graminis f. sp. tritici, (the causal agent of wheatpowdery mildew) and incubated in a growth chamber at 20° C. for 7 days,after which disease ratings were made.

Test B

The test suspension was sprayed to the point of run-off on wheatseedlings. The following day the seedlings were inoculated with a sporesuspension of Puccinia recondita (the causal agent of wheat leaf rust)and incubated in a saturated atmosphere at 20° C. for 24 h, and thenmoved to a growth chamber at 20° C. for 6 days, after which diseaseratings were made.

Test C

The test suspension was sprayed to the point of run-off on riceseedlings. The following day the seedlings were inoculated with a sporesuspension of Pyricularia oryzae (the causal agent of rice blast) andincubated in a saturated atmosphere at 27° C. for 24 h, and then movedto a growth chamber at 30° C. for 5 days, after which disease ratingswere made.

Test D

The test suspension was sprayed to the point of run-off on tomatoseedlings. The following day the seedlings were inoculated with a sporesuspension of Phytophthora infestans (the causal agent of potato andtomato late blight) and incubated in a saturated atmosphere at 20° C.for 24 h, and then moved to a growth chamber at 20° C. for 5 days, afterwhich disease ratings were made.

Test E

The test suspension was sprayed to the point of run-off on grapeseedlings. The following day the seedlings were inoculated with a sporesuspension of Plasmopara viticola (the causal agent of grape downymildew) and incubated in a saturated atmosphere at 20° C. for 24 h,moved to a growth chamber at 20° C. for 6 days, and then incubated in asaturated atmosphere at 20° C. for 24 h, after which disease ratingswere made.

Test F

The test suspension was sprayed to the point of run-off on cucumberseedlings. The following day the seedlings were inoculated with a sporesuspension of Botrytis cinerea (the causal agent of gray mold on manycrops) and incubated in a saturated atmosphere at 20° C. for 48 h, andmoved to a growth chamber at 20° C. for 5 days, after which diseaseratings were made.

Results for Tests A-F are given in Table A. In the table, a rating of100 indicates 100% disease control and a rating of 0 indicates nodisease control (relative to the controls). A dash (-) indicates no testresults.

                  TABLE A                                                         ______________________________________                                        Cmpd No.                                                                             Test A   Test B  Test C                                                                              Test D Test E                                                                              Test F                             ______________________________________                                         1     100      100     94     0     16*   41                                    2 100  93  0 24  0* 41                                                        3 46  0  0  0 13*  0                                                          4 100  100  97  0 17* 66                                                      5 97 100   0 --  0*  0                                                        6 97 100  52  0 17* 41                                                        7 97 100  86  0  8* 42                                                        8 99 97 74 10 21*  0                                                          9 91 99 53 86 49*  0                                                         10 82 97 32 72  6**  0                                                        11 100  99 53 91 100** 82                                                     12 100  100  53 39 95* 43                                                     13 100  100  91 73 88* 67                                                     14 100  100  85 56 28* 82                                                     15 94 99 26  0 42* 82                                                         16 99 97 26  0 40* 90                                                         17 98 99 90  0 48* 69                                                         18 53 61  0  0 30*  0                                                         19 91  0  0 22  0*  0                                                         20 59 84  0  0  8*  0                                                         21 31 93  0  0 29*  0                                                         22 91 66  0  0  0*  0                                                         23  0  0  0  0  3*  0                                                         24  0  0  0  0  3*  0                                                         25 98 97  0  0 22* 46                                                         26 99 100   0  0  2* 10                                                       27 76 99  0  0  2*  0                                                         28 100  100  32  0 14* 90                                                     29 100  100  53  0 23* 48                                                     30 99 99 53  0  7* 70                                                         31 60  0  0  0  7* 68                                                         32  0  0  0  0  7* 44                                                         33 97 85  0 46  6*  0                                                         34  0 66  0 25 13* 57                                                         35 36 66  0 11  7*  0                                                         36 84 85  0 25  9*  0                                                         37 25 93 53 25  0*  0                                                         38 91 99 60 95 71* 77                                                         39 61 86 74  0 --  0                                                          40 61 85  0 26  2* 44                                                         41  0 65  0  0 --  0                                                          42 55 100  53 25  1*  5                                                       43 100  99 32 -- 11* 68                                                       44 100  100  32 10  1* 94                                                     45 100  99 53 72  1* 94                                                       46 99 100  32 24 19* 46                                                       47  0  0  0  0 37*  0                                                         48 98 99 32 26 15* 41                                                         49 99 94 53 72 12*  7                                                         50 94 67  0 63  5* 94                                                         51 85  0  0 16 --  0                                                          52 85 26  0 42 --  0                                                          53 57 86  0  0  5*  0                                                       ______________________________________                                         *Compound was tested at 10 ppm (equivalent to 25 g/ha).                       **Compound was tested at 40 ppm (equivalent to 100 g/ha).                

What is claimed is:
 1. A compound selected from Formula I, N-oxides andagriculturally suitable salts thereof, ##STR115## wherein: E is a ringsystem selected fromi) 5 to 12-membered monocyclic and fused bicyclicaromatic heterocyclic ring systems, each heterocyclic ring systemcontaining 1 to 6 heteroatoms independently selected from the groupnitrogen, oxygen, and sulfur, provided that each heterocyclic ringsystem contains no more than 4 nitrogens, no more than 2 oxygens, and nomore than 2 sulfurs, and each fused bicyclic ring system does or doesnot contain one nonaromatic ring that does or does not include one ortwo Q as ring members and does or does not include one or two ringmembers independently selected from C(═O) and S(O)₂, provided that G isattached to an aromatic ring, and when G and Y are attached to the samering, then G and Y are attached to adjacent ring members, each aromaticheterocyclic ring system unsubstituted or substituted with one of R³,R⁴, or both R³ and R⁴ ; A is O; S; N; NR⁵ ; or CR¹⁴ ; G is C or N;provided that when G is C, then A is O, S or NR⁵ and the floating doublebond is attached to G; and when G is N, then A is N or CR¹⁴ and thefloating double bond is attached to A; W is O; S; NH; N(C₁ -C₆ alkyl);or NO(C₁ -C₆ alkyl); X is OR¹ ; S(O)_(m) R¹ ; or halogen; R¹ is C₁ -C₆alkyl; C₁ -C₆ haloalkyl; C₂ -C₆ alkenyl; C₂ -C₆ haloalkenyl; C₂ -C₆alkynyl; C₂ -C₆ haloalkynyl; C₃ -C₆ cycloalkyl; C₂ -C₄ alkylcarbonyl; orC₂ -C₄ alkoxycarbonyl; R² is H; C₁ -C₆ alkyl; C₁ -C₆ haloalkyl; C₂ -C₆alkenyl; C₂ -C₆ haloalkenyl; C₂ -C₆ alkynyl; C₂ -C₆ haloalkynyl; C₃ -C₆cycloalkyl; C₂ -C₄ alkylcarbonyl; C₂ -C₄ alkoxycarbonyl; hydroxy; C₁ -C₂alkoxy; or acetyloxy; R³ and R⁴ are each independently halogen; cyano;nitro; hydroxy; C₁ -C₆ alkyl; C₁ -C₆ haloalkyl; C₂ -C₆ alkenyl; C₂ -C₆haloalkenyl; C₂ -C₆ alkynyl; C₂ -C₆ haloalkynyl; C₁ -C₆ alkoxy; C₁ -C₆haloalkoxy; C₂ -C₆ alkenyloxy; C₂ -C₆ alkynyloxy; C₁ -C₆ alkylthio; C₁-C₆ alkylsulfinyl; C₁ -C₆ alkylsulfonyl; formyl; C₂ -C₆ alkylcarbonyl;C₂ -C₆ alkoxycarbonyl; NH₂ C(O); (C₁ -C₄ alkyl)NHC(O); (C₁ -C₄ alkyl)₂NC(O); Si(R²⁵)₃ ; Ge(R²⁵)₃ ; (R²⁵)₃ Si--C.tbd.C--; or phenyl,phenylethynyl, benzoyl, or phenylsulfonyl each substituted with R⁸ andunsubstituted or substituted with one or more R¹⁰ ; R⁵ is H; C₁ -C₆alkyl; C₁ -C₆ haloalkyl; C₂ -C₆ alkenyl; C₂ -C₆ haloalkenyl; C₂ -C₆alkynyl; C₂ -C₆ haloalkynyl; C₃ -C₆ cycloalkyl; C₂ -C₄ alkylcarbonyl; orC₂ -C₄ alkoxycarbonyl; Y is --O--; --S(O)_(n) --; --NR¹⁵ --; --C(═O)--;--CH(OR¹⁵)--; --CHR⁶ --; --CHR⁶ CHR⁶ --; --CR⁶ ═CR⁶ --; --C.tbd.C--;--CHR¹⁵ O--; --OCHR¹⁵ --; --CHR¹⁵ S(O)_(n) --; --S(O)_(n) CHR¹⁵ --;--CHR¹⁵ O--N═C(R⁷)--; --(R⁷)C═N--OCH(R¹⁵)--; --C(R⁷)═N--O--;--O--N═C(R⁷)--; --CHR¹⁵ OC(═O)N(R¹⁵)--; --CHR¹⁵ OC(═S)N(R¹⁵)--; --CHR¹⁵OC(═O)O--; --CHR¹⁵ OC(═S)O--; --CHR¹⁵ OC(═O)S--; --CHR¹⁵ OC(═S)S--;--CHR¹⁵ SC(═O)N(R¹⁵)--; --CHR¹⁵ SC(═S)N(R¹⁵)--; --CHR¹⁵ SC(═O)O--;--CHR¹⁵ SC(═S)O--; --CHR¹⁵ SC(═O)S--; --CHR¹⁵ SC(═S)S--; --CHR¹⁵SC(═NR¹⁵)S--; --CHR¹⁵ N(R¹⁵)C(═O)N(R¹⁵)--; --CHR¹⁵O--N(R¹⁵)C(═O)N(R¹⁵)--; --CHR¹⁵ O--N(R¹⁵)C(═S)N(R¹⁵)--; --CHR¹⁵O--N═C(R⁷)NR¹⁵ --; --CHR¹⁵ O--N═C(R⁷)OCH₂ --; --CHR¹⁵ O--N═C(R⁷)--N═N--;--CHR¹⁵ O--N═C(R⁷)--C(═O)--; --CHR¹⁵ O--N═C(R⁷)--C(═N--A² --Z¹)--A¹ --;--CHR¹⁵ O--N═C(R⁷)--C(R⁷)═N--A² --A³ --; --CHR¹⁵ O--N═C(--C(R⁷)═N--A²--Z¹)--; --CHR¹⁵ O--N═C(R⁷)--CH₂ O--; --CHR¹⁵ O--N═C(R⁷)--CH₂ S--;--O--CH₂ CH₂ O--N═C(R⁷)--; --CHR¹⁵ O--C(R¹⁵)═C(R⁷)--; --CHR¹⁵O--C(R⁷)═N--; --CHR¹⁵ S--C(R⁷)═N--; --C(R⁷)═N--NR¹⁵ --;--CH═N--N═C(R⁷)--; --CHR¹⁵ N(R¹⁵)--N═C(R⁷)--; --CHR¹⁵N(COCH₃)--N═C(R⁷)--; --OC(═S)NR¹⁵ C(═O)--; --CHR⁶ --C(═W¹)--A¹ --;--CHR⁶ CHR⁶ --C(═W¹)--A¹ --; --CR⁶ ═CR⁶ --C(═W¹)--A¹ --;--C.tbd.--C--C(═W¹)--A¹ --; --N═CR⁶ --C(═W¹)--A¹ --; or a direct bond;and the directionality of the Y linkage is defined such that the moietydepicted on the left side of the linkage is bonded to E and the moietyon the right side of the linkage is bonded to Z; Z¹ is H or --A³ --Z; W¹is O or S; A¹ is O; S; NR¹⁵ ; or a direct bond; A² is O; NR¹⁵ ; or adirect bond; A³ is --C(═O)--; --S(O)₂ --; or a direct bond; each R⁶ isindependently H; 1-2 CH₃ ; C₂ -C₃ alkyl; C₁ -C₃ alkoxy; C₃ -C₆cycloalkyl; formylamino; C₂ -C₄ alkylcarbonylamino; C₂ -C₄alkoxycarbonylamino; NH₂ C(O)NH; (C₁ -C₃ alkyl)NHC(O)NH; (C₁ -C₃ alkyl)₂NC(O)NH; N(C₁ -C₃ alkyl)₂ ; piperidinyl; morpholinyl; 1-2 halogen;cyano; or nitro; each R⁷ is independently H; C₁ -C₆ alkyl; C₁ -C₆haloalkyl; C₁ -C₆ alkoxy; C₁ -C₆ haloalkoxy; C₁ -C₆ alkylthio; C₁ -C₆alkylsulfinyl; C₁ -C₆ alkylsulfonyl; C₁ -C₆ haloalkylthio; C₁ -C₆haloalkylsulfinyl; C₁ -C₆ haloalkylsulfonyl; C₂ -C₆ alkenyl; C₂ -C₆haloalkenyl; C₂ -C₆ alkynyl; C₂ -C₆ haloalkynyl; C₃ -C₆ cycloalkyl; C₂-C₄ alkylcarbonyl; C₂ -C₄ alkoxycarbonyl; halogen; cyano; nitro;hydroxy; amino; NH(C₁ -C₆ alkyl); N(C₁ -C₆ alkyl)₂ ; or morpholinyl;each Z is independently selected fromi) C₁ -C₁₀ alkyl, C₂ -C₁₀ alkenyl,and C₂ -C₁₀ alkynyl each substituted with R⁹ and unsubstituted orsubstituted with one or more R¹⁰ ; ii) C₃ -C₈ cycloalkyl, C₃ -C₈cycloalkenyl and phenyl each substituted with R⁹ and unsubstituted orsubstituted with one or more R¹⁰ ; iii) a ring system selected from 3 to14-membered monocyclic, fused bicyclic and fused tricyclic nonaromaticheterocyclic ring systems and 5 to 14-membered monocyclic, fusedbicyclic and fused tricyclic aromatic heterocyclic ring systems, eachheterocyclic ring system containing 1 to 6 heteroatoms independentlyselected from the group nitrogen, oxygen, and sulfur, provided that eachheterocyclic ring system contains no more than 4 nitrogens, no more than2 oxygens, and no more than 2 sulfurs, each nonaromatic or aromaticheterocyclic ring system substituted with R⁹ and unsubstituted orsubstituted with one or more R¹⁰ ; iv) a multicyclic ring systemselected from 8 to 14-membered fused-bicyclic and fused-tricyclic ringsystems which are an aromatic carbocyclic ring system, a nonaromaticcarbocyclic ring system, or a ring system containing one or twononaromatic rings that each include one or two Q as ring members and oneor two ring members independently selected from C(═O) and S(O)₂, and anyremaining rings as aromatic carbocyclic rings, each multicyclic ringsystem substituted with R⁹ and unsubstituted or substituted with one ormore R¹⁰ ; and v) adamantyl substituted with R⁹ and unsubstituted orsubstituted with one or more R¹⁰ ; each Q is independently selected fromthe group --CHR¹³ --, --NR¹³ --, --O--, and --S(O)_(p) --; R⁸ is H; 1-2halogen; C₁ -C₆ alkyl; C₁ -C₆ haloalkyl; C₁ -C₆ alkoxy; C₁ -C₆haloalkoxy; C₂ -C₆ alkenyl; C₂ -C₆ haloalkenyl; C₂ -C₆ alknyl; C₁ -C₆alkylthio; C₁ -C₆ haloalkylthio; C₁ -C₆ alkylsulfinyl; C₁ -C₆alkylsulfonyl; C₃ -C₆ cycloalkyl; C₃ -C₆ alkenyloxy; CO₂ (C₁ -C₆ alkyl);NH(C₁ -C₆ alkyl); N(C₁ -C₆ alkyl)₂ ; cyano; nitro; SiR¹⁹ R²⁰ R²¹ ; orGeR¹⁹ R²⁰ R²¹ ; R⁹ is H; 1-2 halogen; C₁ -C₆ alkyl; C₁ -C₆ haloalkyl; C₁-C₆ alkoxy; C₁ -C₆ haloalkoxy; C₂ -C₆ alkenyl; C₂ -C₆ haloalkenyl; C₂-C₆ alkynyl; C₁ -C₆ alkylthio; C₁ -C₆ haloalkylthio; C₁ -C₆alkylsulfinyl; C₁ -C₆ alkylsulfonyl; C₃ -C₆ cycloalkyl; C₃ -C₆alkenyloxy; CO₂ (C₁ -C₆ alkyl); NH(C₁ -C₆ alkyl); N(C₁ -C₆ alkyl)₂ ;--C(R¹⁸)═NOR¹⁷ ; cyano; nitro; SF₅ ; SiR²² R²³ R²⁴ ; or GeR²² R²³ R²⁴ ;or R⁹ is phenyl, benzyl, benzoyl, phenoxy, pyridinyl, pyridinyloxy,thienyl, thienyloxy, furanyl, pyrimidinyl, or pyrimidinyloxy eachunsubstituted or substituted with one of R¹¹, R¹², or both R¹¹ and R¹² ;each R¹⁰ is independently halogen; C₁ -C₄ alkyl; C₁ -C₄ haloalkyl; C₁-C₄ alkoxy; nitro; or cyano; or when R⁹ and an R¹⁰ are attached toadjacent atoms on Z, R⁹ and said adjacently attached R¹⁰ when takentogether form --OCH₂ O-- or --OCH₂ CH₂ O--; each CH₂ group of said takentogether R⁹ and R¹⁰ unsubstituted or substituted with 1-2 halogen; orwhen Y and an R¹⁰ are attached to adjacent atoms on Z and Y is --CHR¹⁵O--N═C(R⁷)--, --O--N═C(R⁷)--, --O--CH₂ CH₂ O--N═C(R⁷)--, --CHR¹⁵O--C(R¹⁵)═C(R⁷)--, --CH═N--N═C(R⁷)--, --CHR¹⁵ N(R¹⁵)--N═C(R⁷)-- or--CHR¹⁵ N(COCH₃)--N═C(R⁷)--, R⁷ and said adjacently attached R¹⁰ whentaken together form --(CH₂)_(r) --J-- such that J is attached to Z; J is--CH₂ --; --CH₂ CH₂ --; --OCH₂ --; --CH₂ O--; --SCH₂ --; --CH₂ S--;--N(R¹⁶)CH₂ --; or --CH₂ N(R¹⁶)--; each CH₂ group of said Junsubstituted or substituted with 1 to 2 CH₃ ; R¹¹ and R¹² are eachindependently halogen; C₁ -C₄ alkyl; C₁ -C₄ haloalkyl; C₁ -C₄ alkoxy; C₁-C₄ haloalkoxy; nitro; cyano; Si(R²⁵)₃ ; or Ge(R²⁵)₃ ; each R¹³ isindependently H; C₁ -C₆ alkyl; C₁ -C₆ haloalkyl; or phenyl unsubstitutedor substituted with halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄alkoxy, C₁ -C₄ haloalkoxy, nitro or cyano; R¹⁴ is H; halogen; C₁ -C₆alkyl; C₁ -C₆ haloalkyl; C₂ -C₆ alkenyl; C₂ -C₆ haloalkenyl; C₂ -C₆alkynyl; C₂ -C₆ haloalkynyl; or C₃ -C₆ cycloalkyl; each R¹⁵ isindependently H; C₁ -C₃ alkyl; C₃ -C₆ cycloalkyl; or phenyl or benzyl,each unsubstituted or substituted on the phenyl ring with halogen, C₁-C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, nitro orcyano; or when Y is --CHR¹⁵ N(R¹⁵)C(═O)N(R⁵)--, the two R¹⁵ attached tonitrogen atoms on said group when taken together form --(CH₂)_(s) --; orwhen Y is --CHR¹⁵ O--N═C(R⁷)NR¹⁵ --, R⁷ and the adjacently attached R¹⁵when taken together form --CH₂ --(CH₂)_(s) --; --O--(CH₂)_(s) --;--S--(CH₂)_(s) --; or --N(C₁ -C₃ alkyl)--(CH₂)_(s) --; with thedirectionality of said linkage defined such that the moiety depicted onthe left side of the linkage is bonded to the carbon and the moiety onthe right side of the linkage is bonded to the nitrogen; R¹⁶, R¹⁷, andR¹⁸ are each independently H; C₁ -C₃ alkyl; C₃ -C₆ cycloalkyl; or phenylunsubstituted or substituted with halogen, C₁ -C₄ alkyl, C₁ -C₄haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, nitro or cyano; R¹⁹, R²⁰,R²¹, R²², R²³, and R²⁴ are each independently C₁ -C₆ alkyl; C₂ -C₆alkenyl; C₁ -C₄ alkoxy; or phenyl; each R²⁵ is independently C₁ -C₄alkyl; C₁ -C₄ haloalkyl; C₂ -C₄ alkenyl; C₁ -C₄ alkoxy; or phenyl; m, nand p are each independently 0, 1 or 2; r is 0 or 1; and s is 2 or
 3. 2.A compound of claim 1, whereinE is selected from the group1H-pyrrole-1,2-, 2,3- and 3,4-diyl; 2,3- and 3,4-furandiyl; 2,3- and3,4-thiophenediyl; 1H-pyrazole-1,5-, 3,4- and 4,5-diyl;1H-imidazole-1,2-, 4,5- and 1,5-diyl; 3,4- and 4,5-isoxazolediyl;4,5-oxazolediyl; 3,4- and 4,5-isothiazolediyl; 4,5-thiazolediyl;1H-1,2,3-triazole-1,5- and 4,5-diyl; 2H-1,2,3-triazole-4,5-diyl;1H-1,2,4-triazole-1,5-diyl; 4H-1,2,4-triazole-3,4-diyl;1,2,3-oxadiazole-4,5-diyl; 1,2,5-oxadiazole-3,4-diyl;1,2,3-thiadiazole-4,5-diyl; 1,2,5-thiadiazole-3,4-diyl;1H-tetrazole-1,5-diyl; 2,3- and 3,4-pyridinediyl; 3,4- and4,5-pyridazinediyl; 4,5-pyrimidinediyl; 2,3-pyrazinediyl;1,2,3-triazine-4,5-diyl; 1,2,4-triazine-5,6-diyl; 1H-indole-1,4-,1,5-,1,6-, 1,7-, 2,4-, 2,5-, 2,6-, 2,7-, 3,4-, 3,5-, 3,6-, 3,7-, 1,2-,2,3-, 4,5-, 5,6- and 6,7-diyl; 2,4-, 2,5-, 2,6-, 2,7-, 3,4-, 3,5-, 3,6-,3,7-, 2,3-, 4,5-, 5,6- and 6,7-benzofurandiyl; benzo[b]thiophene-2,4-,2,5-, 2,6-, 2,7-, 3,4-, 3,5-, 3,6-, 3,7-, 2,3-, 4,5-, 5,6- and 6,7-diyl;1H-indazole-1,4-, 1,5-, 1,6-, 1,7-, 3,4-, 3,5-, 3,6-, 3,7-, 4,5-, 5,6-and 6,7-diyl; 1H-benzimidazole-1,4-, 1,5-, 1,6-, 1,7-, 2,4-, 2,5-, 2,6-,2,7-, 4,5-, 5,6- and 6,7-diyl; 1,2-benzisoxazole-3,4-, 3,5-, 3,6-, 3,7-,4,5-, 5,6- and 6,7-diyl; 2,4-, 2,5-, 2,6-, 2,7-, 4,5-, 5,6- and6,7-benzoxazolediyl; 1,2-benzisothiazole-3,4-, 3,5-, 3,6-, 3,7-, 4,5-,5,6- and 6,7-diyl; 2,4-, 2,5-, 2,6-, 2,7-, 4,5-, 5,6- and6,7-benzothiazolediyl; 2,5-, 2,6-, 2,7-, 2,8-, 3,5-, 3,6-, 3,7-, 3,8-,4,5-, 4,6-, 4,7-, 4,8-, 2,3-, 3,4-, 5,6-, 6,7- and 7,8-quiolinediyl;1,5-, 1,6-, 1,7-, 1,8-, 3,5-, 3,6-, 3,7-, 3,8-, 4,5-, 4,6-, 4,7-, 4,8-,3,4-, 5,6-, 6,7- and 7,8-isoquinolinediyl; 3,5-, 3,6-, 3,7-, 3,8-, 4,5-,4,6-, 4,7-, 4,8-, 3,4-, 5,6-, 6,7- and 7,8-cinnolinediyl; 1,5-, 1,6-,1,7-, 1,8-, 5,6-, 6,7- and 7,8-phthalazinediyl; 2,5-, 2,6-, 2,7-, 2,8-,4,5-, 4,6-, 4,7-, 4,8-, 5,6-, 6,7- and 7,8-quinazolinediyl; 2,5-, 2,6-,2,7-, 2,8-, 2,3-, 5,6-, 6,7- and 7,8-quinoxalinediyl;1,8,-naphthyridine-2,5-, 2,6-, 2,7-, 3,5-, 3,6-, 4,5-, 2,3- and3,4-diyl; 2,6-, 2,7-, 4,6-, 4,7-, 6,7-pteridinediyl;pyrazolo[5,1-b]thiazole-2,6-, 2,7-, 3,6-, 3,7-, 2,3- and 6,7-diyl;thiazolo[2,3-c]-1,2,4-triazole-2,5-, 2,6-, 5,6-diyl;2-oxo-1,3-benzodioxole-4,5- and 5,6-diyl; 1,3-dioxo-1H-isoindole-2,4-,2,5-, 4,5- and 5,6-diyl; 2-oxo-2H-1-benzopyran-3,5-, 3,6-, 3,7-, 3,8-,4,5-, 4,6-, 4,7-, 4,8-, 5,6-, 6,7- and 7,8-diyl;[1,2,4]triazolo[1,5-a]pyridine-2,5-, 2,6-, 2,7-, 2,8-, 5,6-, 6,7- and7,8-diyl; 3,4-dihydro-2,4-dioxo-2H-1,3-benzoxazine-3,5-, 3,6-, 3,7-,3,8-, 5,6-, 6,7- and 7,8-diyl; 2,3-dihydro-2-oxo-3,4-, 3,5-, 3,6-, 3,7-,4,5-, 5,6- and 6,7-benzofurandiyl; thieno[3,2-d]thiazole-2,5-, 2,6-, and5,6-diyl; 5,6,7,8-tetrahydro-2,5-, 2,6-, 2,7-, 2,8-, 3,5-, 3,6-, 3,7-,3,8-, 4,5-, 4,6-, 4,7-, 4,8-, 2,3- and 3,4-quinolinediyl;2,3-dihydro-1,1,3-trioxo-1,2-benzisothiazole-2,4-, 2,5-, 2,6-, 2,7-,4,5-, 5,6- and 6,7-diyl; 1,3-benzodioxole-2,4-, 2,5-, 4,5- and 5,6-diyl;2,3-dihydro-2,4-, 2,5-, 2,6-, 2,7-, 3,4-, 3,5-, 3,6-, 3,7-, 4,5-, 5,6-and 6,7-benzofurandiyl; 2,3-dihydro-1,4-benzodioxin-2,5-, 2,6-, 2,7-,2,8-, 5,6- and 6,7-diyl;5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-2,4-, 2,5-, 2,6-, 2,7-,2,8-, 3,4-, 3,5-, 3,6-, 3,7-, 3,8-, and 2,3-diyl; each aromatic ringsystem unsubstituted or substituted with one of R³, R⁴, or both R³ andR⁴ ; W is O; R¹ is C₁ -C₃ alkyl or C₁ -C₃ haloalkyl; R² is H; C₁ -C₆alkyl; C₁ -C₆ haloalkyl; or C₃ -C₆ cycloalkyl; R³ and R⁴ are eachindependently halogen; cyano; nitro; C₁ -C₆ alkyl; C₁ -C₆ haloalkyl; C₁-C₆ alkoxy; C₁ -C₆ haloalkoxy; C₁ -C₆ alkylthio; C₁ -C₆ alkylsulfonyl;C₂ -C₆ alkylcarbonyl; C₂ -C₆ alkoxycarbonyl; (C₁ -C₄ alkyl)NHC(O); (C₁-C₄ alkyl)₂ NC(O); benzoyl; or phenylsulfonyl; Y is --O--; --CH═CH--;--C.tbd.C--; --CH₂ O--; --OCH₂ --; --CH₂ S(O)_(n) --; --CH₂O--N═C(R⁷)--; --(R⁷)C═N--OCH(R¹⁵)--; --C(R⁷)═N--O--; --CH₂ OC(O)NH--;--CH₂ S--C(R⁷)═N--; --CH═CR⁶ --C(═W¹)--A¹ --; or a direct bond; R⁷ is H;C₁ -C₆ alkyl; C₁ -C₆ haloalkyl; C₁ -C₆ alkoxy; C₁ -C₆ alkylthio; C₂ -C₆C₂ -C₆ alkynyl; C₃ -C₆ cycloalkyl; halogen; or cyano; or when Y and anR¹⁰ are attached to adjacent atoms on Z and Y is --CH₂ O--N═C(R⁷)--, R⁷and said adjacently attached R¹⁰ when taken together form --(CH₂)_(r)--J-- such that J is attached to Z; Z is selected from the group C₁ -C₁₀alkyl; C₃ -C₈ cycloalkyl; phenyl; naphthalenyl; anthracenyl;phenanthrenyl; 1H-pyrrolyl; furanyl; thienyl; 1H-pyrazolyl;1H-imidazolyl; isoxazolyl; oxazolyl; isothiazolyl; thiazolyl;1H-1,2,3-triazolyl; 2H-1,2,3-triazolyl; 1H-1,2,4-triazolyl;4H-1,2,4-triazolyl; 1,2,3-oxadiazolyl; 1,2,4-oxadiazolyl;1,2,5-oxadiazolyl; 1,3,4-oxadiazolyl; 1,2,3-thiadiazolyl;1,2,4-thiadiazolyl; 1,2,5-thiadiazolyl; 1,3,4-thiadiazolyl;1H-tetrazolyl; 2H-tetrazolyl; pyridinyl; pyridazinyl; pyrimidinyl;pyrazinyl; 1,3,5-triazinyl; 1,2,4-triazinyl; 1,2,4,5-tetrazinyl;1H-indolyl; benzofuranyl; benzo[b]thiophenyl; 1H-indazolyl;1H-benzimidazolyl; benzoxazolyl; benzothiazolyl; quinolinyl;isoquinolinyl; cinnolinyl; phthalazinyl; quinazolinyl; quinoxalinyl;1,8-naphthyridinyl; pteridinyl; 2,3-dihydro-1H-indenyl;1,2,3,4-tetrahydronaphthalenyl;6,7,8,9-tetrahydro-5H-benzocycloheptenyl;5,6,7,8,9,10-hexahydrobenzocyclooctenyl; 2,3-dihydro-3-oxobenzofuranyl;1,3-dihydro-1-oxoisobenzofiuranyl; 2,3-dihydro-2-oxobenzofuranyl;3,4-dihydro-4-oxo-2H-1-benzopyranyl;3,4-dihydro-1-oxo-1H-2-benzopyranyl;3,4-dihydro-3-oxo-1H-2-benzopyranyl;3,4-dihydro-2-oxo-2H-1-benzopyranyl; 4-oxo-4H-1-benzopyranyl;2-oxo-2H-1-benzopyranyl; 2,3,4,5-tetrahydro-5-oxo-1-benzoxepinyl;2,3,4,5-tetrahydro-2-oxo-1-benzoxepinyl;2,3-dihydro-1,3-dioxo-1H-isoindolyl;1,2,3,4-tetrahydro-1,3-dioxoisoquinolinyl;3,4-dihydro-2,4-dioxo-2H-1,3-benzoxazinyl; 2-oxo-1,3-benzodioxyl;2,3-dihydro-1,1,3-trioxo-1,2-benzisothiazolyl; 9H-fluorenyl; azulenyl;and thiazolo[2,3-c]-1,2,4-triazolyl; each group substituted with R⁹ andunsubstituted or substituted with one or more R¹⁰ ; R⁹ is H; 1-2halogen; C₁ -C₆ alkyl; C₁ -C₆ haloalkyl; C₁ -C₆ alkoxy; C₁ -C₆haloalkoxy; C₁ -C₆ alkylthio; cyano; CO₂ (C₁ -C₆ alkyl); NH(C₁ -C₆alkyl); N(C₁ -C₆ alkyl)₂ ; SiR²² R²³ R²⁴ ; or GeR²² R²³ R²⁴ ; or R⁹ isC₃ -C₆ cycloalkyl, phenyl, phenoxy, pyridinyl, pyridinyloxy,pyrimidinyl, or pyrimidinyloxy, each unsubstituted or substituted withone of R¹¹, R¹², or both R¹¹ and R¹² ; and each R¹⁵ is independently H;C₁ -C₃ alkyl; or C₃ -C₆ cycloalkyl.
 3. A compound of claim 2 whereinE isselected from the group 2,3- and 3,4-furandiyl; 2,3- and3,4-thiophenediyl; 2,3- and 3,4-pyridinediyl; 4,5-pyrimidinediyl; 2,4-,2,7-, 3,5-, 2,3-, 4,5-, 5,6- and 6,7-benzofurandiyl;benzo[b]thiophene-2,4-, 2,7-, 3,5-, 2,3-, 4,5-, 5,6- and 6,7-diyl; eacharomatic ring system unsubstituted or substituted with one of R³, R⁴, orboth R³ and R⁴ ; Z is selected from the group phenyl;1,2,4-thiadiazolyl; pyridinyl; pyrimidinyl; and naphthalenyl; each groupsubstituted with R⁹ and unsubstituted or substituted with one or moreR¹⁰ ; R⁷ is H; C₁ -C₆ alkyl; C₁ -C₆ haloalkyl; C₁ -C₆ alkoxy; C₁ -C₆alkylthio; C₂ -C₆ alkenyl; C₂ -C₆ alkynyl; cyclopropyl; halogen; orcyano; or when Y and an R¹⁰ are attached to adjacent atoms on Z and Y is--CH₂ O--N═C(R⁷)--, R⁷ and said adjacently attached R¹⁰ when takentogether form --(CH₂)_(r) --J-- such that J is attached to Z; J is --CH₂-- or --CH₂ CH₂ --; and r is
 1. 4. A compound of claim 3 wherein:A is O;N; NR⁵ ; or CR¹⁴ ; X is OR¹ ; R¹ is C₁ -C₃ alkyl; R² is H or C₁ -C₂alkyl; Y is --O--; --CH═CH--; --CH₂ O--; --CH₂ O--N═C(R⁷)--;--(R⁷)C═N--OCH(R¹⁵)--; --CH₂ OC(═O)NH--; --CH₂ S--C(R⁷)═N--; or --CH═CR⁶--C(═W¹)--A¹ --; R⁷ is H; C₁ -C₃ alkyl; C₁ -C₃ haloalkyl; C₁ -C₃ alkoxy;C₁ -C₃ alkylthio; or cyclopropyl; and each R¹⁵ is independently H; C₁-C₃ alkyl; or cyclopropyl.
 5. A compound of claim 4 wherein:A is O orNR⁵ ; G is C; and Y is --O--; --CH₂ O--; or --CH₂ O--N═C(R⁷)--.
 6. Acompound of claim 5 wherein:R¹ is methyl; and R² is methyl.
 7. Acompound of claim 4 wherein:A is N or CR¹⁴ ; G is N; and Y is --O--;--CH₂ O--; or --CH₂ O--N═C(R⁷)--.
 8. A compound of claim 7 wherein:R¹ ismethyl; and R² is methyl.
 9. The compound of claim 4 which is selectedfrom thegroup:2,4-dihydro-5-methoxy-2-methyl-4-[2-[[[[1-[3-(trimethylsilyl)phenyl]ethylidene]amino]oxy]methyl]-3-thienyl]-3H-1,2,4-triazol-3-one;2,4-dihydro-5-methoxy-2-methyl-4-[2-[[[[1-[3-(trifluoromethyl)phenyl]ethylidene]amino]oxy]methyl]-3-thienyl]-3H-1,2,4-triazol-3one;4-[2-[(2,5-dimethylphenoxy)methyl]-3-thienyl]-2,4-dihydro-5-methoxy-2-methyl-3H-1,2,4-triazol-3-one;(1,1-dimethylethyl)2-chloro-3-[3-(1,5-dihydro-3-methoxy-1-methyl-5-oxo-4H-1,2,4-triazol-4-yl)--2-thienyl]-2-propenoate;4-[2-[[[3-(4-chlorophenyl)-1,2,4-thiadiazol-5-yl]oxy]methyl]-3-thienyl]-2,4-dihydro-5-methoxy-2-methyl-3H-1,2,4-triazol-3-one;and2,4-dihydro-5-methoxy-2-methyl-4-[2-[[[3-[4-(trifluoromethyl)phenyl]-1,2,4-thiadiazol-5-yl]oxy]methyl]-3-thienyl]-3H-1,2,4-triazol-3-one.10. A fungicidal composition comprising a fungicidally effective amountof a compound of claim 1 and at least one of a surfactant, a soliddiluent or a liquid diluent.
 11. A method for controlling plant diseasescaused by fungal plant pathogens comprising applying to the plant orportion thereof, or to the plant seed or seedling, a fungicidallyeffective amount of a compound of claim
 1. 12. A compound selected fromFormula I, N-oxides and agriculturally suitable salts thereof,##STR116## wherein: E is a ring system selected fromi) 5 to 12-memberedmonocyclic and fused bicyclic aromatic heterocyclic ring systems, eachheterocyclic ring system containing 1 to 6 heteroatoms independentlyselected from the group nitrogen, oxygen, and sulfur, provided that eachheterocyclic ring system contains no more than 4 nitrogens, no more than2 oxygens, and no more than 2 sulfurs, and each fused bicyclic ringsystem does or does not contain one nonaromatic ring that does or doesnot include one or two Q as ring members and does or does not includeone or two ring members independently selected from C(═O) and S(O)₂,provided that G is attached to an aromatic ring, and when G and Y areattached to the same ring, then G and Y are attached to adjacent ringmembers, each aromatic heterocyclic ring system unsubstituted orsubstituted with one of R³, R⁴, or both R³ and R⁴ ; A is O; S; N; NR⁵ ;or CR¹⁴ ; G is C or N; provided that when G is C, then A is O, S or NR⁵and the floating double bond is attached to G; and when G is N, then Ais N or CR¹⁴ and the floating double bond is attached to A; W is O; S;NH; N(C₁ -C₆ alkyl); or NO(C₁ -C₆ alkyl); X is OR¹ ; S(O)_(m) R¹ ; orhalogen; R¹ is C₁ -C₆ alkyl; C₁ -C₆ haloalkyl; C₂ -C₆ alkenyl; C₂ -C₆haloalkenyl; C₂ -C₆ alkynyl; C₂ -C₆ haloalkynyl; C₃ -C₆ cycloalkyl; C₂-C₄ alkylcarbonyl; or C₂ -C₄ alkoxycarbonyl; R² is H; C₁ -C₆ alkyl; C₁-C₆ haloalkyl; C₂ -C₆ alkenyl; C₂ -C₆ haloalkenyl; C₂ -C₆ alkynyl; C₂-C₆ haloalkynyl; C₃ -C₆ cycloalkyl; C₂ -C₄ alkylcarbonyl; or C₂ -C₄alkoxycarbonyl; R³ and R⁴ are each independently halogen; cyano; nitro;hydroxy; C₁ C₆ alkyl; C₁ C₆ haloalkyl; C₂ -C₆ alkenyl; C₂ -C₆haloalkenyl; C₂ -C₆ alkynyl; C₂ -C₆ haloalkynyl; C₁ C₆ alkoxy; C₁ C₆haloalkoxy; C₂ -C₆ alkenyloxy; C₂ -C₆ alkynyloxy; C₁ -C₆ alkylthio; C₁C₆ alkylsulfinyl; C₁ -C₆ alkylsulfonyl; formyl; C₂ -C₆ alkylcarbonyl; C₂-C₆ alkoxycarbonyl; NH₂ C(O); (C₁ -C₄ alkyl)NHC(O); (C₁ -C₄ alkyl)₂NC(O); Si(R²⁵)₃ ; Ge(R²⁵)₃ ; (R²⁵)₃ Si--C.tbd.C--; or phenyl,phenylethynyl, benzoyl, or phenylsulfonyl each substituted with R⁸ andunsubstituted or substituted with one or more R¹⁰ ; R⁵ is H; C₁ -C₆alkyl; C₁ -C₆ haloalkyl; C₂ -C₆ alkenyl; C₂ -C₆ haloalkenyl; C₂ -C₆alkynyl; C₂ -C₆ haloalkynyl; C₃ -C₆ cycloalkyl; C₂ -C₄ alkylcarbonyl; orC₂ -C₄ alkoxycarbonyl; Y is --O--; --S(O)n--; --NR¹⁵ --; --C(═O)--;--CH(OR¹⁵)--; --CHR⁶ --; --CHR⁶ CHR⁶ --; --CR⁶ ═CR⁶ --; --C.tbd.C--;--CHR¹⁵ O--; --OCHR¹⁵ --; --CHR¹⁵ S(O)n--; --S(O)nCHR¹⁵ --; --CHR¹⁵O--N═C(R⁷)--; --(R⁷)C═N--OCH(R¹⁵)--; --C(R⁷)═N--O--; --O--N═C(R⁷)--;--CHR¹⁵ OC(═O)N(R¹⁵)--; --CHR⁵ OC(═S)N(R¹⁵)--; --CHR¹⁵O--N(R⁵)C(═O)N(R¹⁵)--; --CHR¹⁵ O--N(R¹⁵)C(═S)N(R¹⁵)--; --CHR¹⁵O--N═C(R⁷)NR¹⁵ --; --CHR¹⁵ O--N═C(R⁷)OCH₂ --; --CHR¹⁵ O--N═C(R⁷)--N═N--;--CHR¹⁵ O--N═C(R⁷)--C(═O)--; --CHR¹⁵ S--C(R⁷)═N--; --C(R⁷)═N--NR¹⁵ --;--CH═N--N═C(R⁷)--; --CHR¹⁵ N(COCH₃)--N═C(R⁷)--; --OC(═S)NR¹⁵ C(═O)--;--CHR⁶ --C(═W¹)--A¹ --; --CHR⁶ CHR⁶ --C(═W¹)--A¹ --; --CR⁶ ═CR⁶--C(═W¹)--A¹ --; --C.tbd.C--C(═W¹)--A¹ --; --N═CR⁶ --C(═W¹)--A¹ --; or adirect bond; and the directionality of the Y linkage is defined suchthat the moiety depicted on the left side of the linkage is bonded to Eand the moiety on the right side of the linkage is bonded to Z; W¹ is Oor S; A¹ is O; S; NR¹⁵ ; or a direct bond; each R⁶ is independently H;1-2 CH₃ ; C₂ -C₃ alkyl; C₁ -C₃ alkoxy; C₃ -C₆ cycloalkyl; formylamino;C₂ -C₄ alkylcarbonylamino; C₂ -C₄ alkoxycarbonylamino; NH₂ C(O)NH; (C₁-C₃ alkyl)NHC(O)NH; (C₁ -C₃ alkyl)₂ NC(O)NH; N(C₁ -C₃ alkyl)₂ ;piperidinyl; morpholinyl; 1-2 halogen; cyano; or nitro; R⁷ is H; C₁ -C₆alkyl; C₁ -C₆ haloalkyl; C₁ -C₆ alkoxy; C₁ -C₆ haloalkoxy; C₁ -C₆alkylthio; C₁ -C₆ alkylsulfinyl; C₁ -C₆ alkylsulfonyl; C₁ -C₆haloalkylthio; C₁ -C₆ haloalkylsulfinyl; C₁ -C₆ haloalkylsulfonyl; C₂-C₆ alkenyl; C₂ -C₆ haloalkenyl; C₂ -C₆ alkynyl; C₂ -C₆ haloalkynyl; C₃-C₆ cycloalkyl; C₂ -C₄ alkylcarbonyl; C₂ -C₄ alkoxycarbonyl; halogen;cyano; or morpholinyl; Z is selected fromi) C₁ -C₁₀ alkyl, C₂ -C₁₀alkenyl, and C₂ -C₁₀ alkynyl each substituted with R⁹ and unsubstitutedor substituted with one or more R¹⁰ ; ii) C₃ -C₈ cycloalkyl and phenyleach substituted with R⁹ and unsubstituted or substituted with one ormore R¹⁰ ; iii) a ring system selected from 3 to 14-membered monocyclic,fused bicyclic and fused tricyclic nonaromatic heterocyclic ring systemsand 5 to 14-membered monocyclic, fused bicyclic and fused tricyclicaromatic heterocyclic ring systems, each heterocyclic ring systemcontaining 1 to 6 heteroatoms independently selected from the groupnitrogen, oxygen, and sulfur, provided that each heterocyclic ringsystem contains no more than 4 nitrogens, no more than 2 oxygens, and nomore than 2 sulfurs, each nonaromatic or aromatic heterocyclic ringsystem substituted with R⁹ and unsubstituted or substituted with one ormore R¹⁰ ; and iv) a multicyclic ring system selected from 8 to14-membered fused-bicyclic and fused-tricyclic ring systems which are anaromatic carbocyclic ring system, a nonaromatic carbocyclic ring system,or a ring system containing one or two nonaromatic rings that eachinclude one or two Q as ring members and one or two ring membersindependently selected from C(═O) and S(O)₂, and any remaining rings asaromatic carbocyclic rings, each multicyclic ring system substitutedwith R⁹ and unsubstituted or substituted with one or more R¹⁰ ; each Qis independently selected from the group --CHR¹³ --, --NR¹³ --, --O--,and --S(O)_(p) --; R⁸ is H; 1-2 halogen; C₁ -C₆ alkyl; C₁ -C₆ haloalkyl;C₁ -C₆ alkoxy; C₁ -C₆ haloalkoxy; C₂ -C₆ alkenyl; C₂ -C₆ haloalkenyl; C₂-C₆ alkynyl; C₁ -C₆ alkylthio; C₁ -C₆ haloalkylthio; C₁ -C₆alkylsulfinyl; C₁ -C₆ alkylsulfonyl; C₃ -C₆ cycloalkyl; C₃ -C₆alkenyloxy; CO₂ (C₁ -C₆ alkyl); NH(C₁ -C₆ alkyl); N(C₁ -C₆ alkyl)₂ ;cyano; nitro; SiR¹⁹ R²⁰ R²¹ ; or GeR¹⁹ R²⁰ R²¹ ; R⁹ is H; 1-2 halogen;C₁ -C₆ alkyl; C₁ -C₆ haloalkyl; C₁ -C₆ alkoxy; C₁ -C₆ haloalkoxyl; C₂-C₆ alkenyl; C₂ -C₆ haloalkenyl; C₂ -C₆ alkynyl; C₁ -C₆ alkylthio; C₁-C₆ haloalkylthio; C₁ -C₆ alkylsulfinyl; C₁ -C₆ alkylsulfonyl; C₃ -C₆cycloalkyl; C₃ -C₆ alkenyloxy; CO₂ (C₁ -C₆ alkyl); NH(C₁ -C₆ alkyl);N(C₁ -C₆ alkyl)₂ ; --C(R¹⁸)═NOR¹⁷ ; cyano; nitro; SF₅ ; SiR²² R²³ R²⁴ ;or GeR²² R²³ R²⁴ ; or R⁹ is phenyl, benzyl, benzoyl, phenoxy, pyridinyl,pyridinyloxy, thienyl, thienyloxy, furanyl, pyrimidinyl, orpyrimidinyloxy each unsubstituted or substituted with one of R¹¹, R¹²,or both R¹¹ and R¹² ; each R¹⁰ is independently halogen; C₁ -C₄ alkyl;C₁ -C₄ haloalkyl; C₁ -C₄ alkoxy; nitro; or cyano; or when R⁹ and an R¹⁰are attached to adjacent atoms on Z, R⁹ and said adjacently attached R¹⁰when taken together form --OCH₂ O-- or --OCH₂ CH₂ O--; each CH₂ group ofsaid taken together R⁹ and R¹⁰ unsubstituted or substituted with 1-2halogen; or when Y and an R¹⁰ are attached to adjacent atoms on Z and Yis --CHR¹⁵ O--N═C(R⁷)--, --O--N═C(R⁷)--, --CH═N--N═C(R⁷)--, or --CHR¹⁵N(COCH₃)--N═C(R⁷)--, R⁷ and said adjacently attached R¹⁰ when takentogether form --(CH₂)_(r) --J-- such that J is attached to Z; J is --CH₂--; --CH₂ CH₂ --; --OCH₂ --; --CH₂ O--; --SCH₂ --; --CH₂ S--;--N(R¹⁶)CH₂ --; or --CH₂ N(R¹⁶)--; each CH₂ group of said Junsubstituted or substituted with 1 to 2 CH₃ ; R¹¹ and R¹² are eachindependently halogen; C₁ -C₄ alkyl; C₁ -C₄ haloalkyl; C₁ -C₄ alkoxy; C₁-C₄ haloalkoxy; nitro; cyano; Si(R²⁵)₃ ; or Ge(R²⁵)₃ ; each R¹³ isindependently H; C₁ -C₆ alkyl; C₁ -C₆ haloalkyl; or phenyl unsubstitutedor substituted with halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄alkoxy, C₁ -C₄ haloalkoxy, nitro or cyano; R¹⁴ is H; halogen; C₁ -C₆alkyl; C₁ -C₆ haloalkyl; C₂ -C₆ alkenyl; C₂ -C₆ haloalkenyl; C₂ -C₆alkynyl; C₂ -C₆ haloalkynyl; or C₃ -C₆ cycloalkyl; each R¹⁵ isindependently H; C₁ -C₃ alkyl; C₃ -C₆ cycloalkyl; or phenyl or benzyl,each unsubstituted or substituted on the phenyl ring with halogen, C₁-C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, nitro orcyano; or when Y is --CHR¹⁵ O--N═C(R⁷)NR¹⁵ --, R⁷ and the adjacentlyattached R¹⁵ when taken together form --CH₂ --(CH₂)_(s) --;--O--(CH₂)_(s) --; --S--(CH₂)_(s) --; or --N(C₁ -C₃ alkyl)--(CH₂)_(s)--; with the directionality of said linkage defined such that the moietydepicted on the left side of the linkage is bonded to the carbon and themoiety on the right side of the linkage is bonded to the nitrogen; R¹⁶,R¹⁷, and R¹⁸ are each independently H; C₁ -C₃ alkyl; C₃ -C₆ cycloalkyl;or phenyl unsubstituted or substituted with halogen, C₁ -C₄ alkyl, C₁-C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, nitro or cyano; R¹⁹,R²⁰, R²¹, R²², R²³, and R²⁴ are each independently C₁ -C₆ alkyl; C₁ -C₄alkoxyl; or phenyl; each R²⁵ is independently C₁ -C₄ alkyl or phenyl; m,n and p are each independently 0, 1 or 2; r is 0 or 1; and s is 2 or 3.13. A compound of claim 1 which is selected from compounds having theformula ##STR117## wherein Y=--CH₂ O--N═C(CH₃)-- and Z=3--(CH₃)₃ Si-Ph;Y=--CH₂ O-- and Z=2,5-diCH₃ -Ph; Y=direct bond and Z=CH₂ Br; Y=--CH₂O--N═C(CH₃)-- and Z=3-CF₃ -Ph; Y=--CH═C(Cl)--C(═O)--O-- and Z=t-Bu;Y=--CH₂ O--N═C(CH₃)-- and Z=4- CF₃ -pyridin-2-yl; Y=direct bond andZ=3-(3-CF₃ -Ph)-1,2,4-oxadiazol-5-yl; Y=--CH₂ O--N═C(CH₃)-- andZ=3,4-diCl-Ph; Y=--CH₂ O--N═C(NH₂)-- and Z=3-CF₃ -Ph; Y=--CH₂O--N═C(CH₃)-- and Z=3,5-diBr-Ph; Y=--CH₂ O--N═C(CH₃)-- andZ=3,5-d.Cl-Ph; Y=--CH₂ O--N═C(CH₃)-- and Z=2-naphthalenyl; Y=--CH₂O--N═C(CH₂ CH₃)-- and Z=3-CF₃ -Ph; Y=--CH₂ O-- andZ=3-(4-Cl-Ph)-1,2,4-thiadiazol-5-yl; Y=--CH₂ O -- andZ=3-(3,5-diCl-Ph)-1,2,4-thiadiazol-5-yl; or Y=--CH₂ O-- and Z=3-(4-CF₃-Ph)-1,2,4-thiadiazol-5-yl.
 14. A compound of claim 1 which is selectedcompounds having the formula ##STR118## wherein Y=direct bond and Z=CH₂Br; Y=--CH₂ O--N═C(CH₃)-- and Z=3,4-diCl-Ph; Y=--CH₂ O--N═C(CH₃)-- andZ=3-(CH₃)₃ Si-Ph; Y=--CH₂ O--N═C(CH₃)-- and Z=4-CF₃ -pyridin-2-yl; orY=--CH₂ O--N═C(CH₃)-- and Z=3-CF₃ -Ph.
 15. A compound of claim 1 whichis selected from compounds having the formula ##STR119## wherein X=Cl,Y=direct bond and Z=CH₃ ; X=CH₃ O, Y=direct bond and Z=CH₃ ; X=CH₃ O,Y=--CH₂ O--N═C(CH₃)-- and Z=3-CF₃ -Ph; X=CH₃ O, Y=--CH₂ O--N═C(CH₃)--and Z=4--CF₃ -pyridin-2-yl; X=CH₃ O, Y=--CH₂ O--N═C(CH₃)-- andZ=3,4-diCl-Ph; X=CH₃ O, Y=--CH₂ O--N═C(CH₃)-- and Z=3-(CH₃)₃ Si-Ph;X=CH₃ O, Y=--CH₂ O--N═C(CH₃)-- and Z=3,5-diCl-Ph; X=CH₃ O, Y=--CH₂O--N═C(CH₃)-- and Z=3,5-diBr-Ph; X=CH₃ O, Y=--CH₂ O--N═C(NH₂)-- andZ=3-CF₃ -Ph; X=CH₃ O, Y=--CH₂ S-- and Z=5-CF₃ -4H-1,2,4-triazol-3-yl;X=CH₃ O, Y=direct bond and Z=3-(3-CF₃ -Ph)-1,2,4-oxadiazol-5-yl; X=CH₃O, Y=--CH₂ -- and Z=3-CF₃ -1H-pyrazol-1-yl; X=CH₃ O, Y=--CH₂ O-- andZ=2-Cl-5-CF₃ -Ph; X=CH₃ O, Y=--CH₂ O-- and Z=2,5-diCH₃ -Ph; X=CH₃ O,Y=--CH₂ O--N═C(CH₃)-- and Z=2-naphthalenyl; X=CH₃ O, Y=--O-- andZ=3-PhO-Ph; or X=Cl, Y=--O-- and Z=3-PhO-Ph.
 16. A compound of claim 1which is selected from compounds having the formula ##STR120## whereinY=direct bond and Z=3-(3-CF₃ -Ph)-1,2,4-oxadiazol-5-yl; Y=direct bondand Z=CH₂ Br; Y=--CH₂ O--N═C(CH₃)-- and Z=2-naphthalenyl; Y=--CH₂O--N═C(CH₃)-- and Z=3,4-diCl-Ph; Y=--CH₂ O--N═C(CH₃)-- and Z=4-CF₃-pyridin-2-yl; Y=--CH₂ O--N═C(CH₃)-- and Z=3,5-diCl-Ph; Y=--CH₂O--N═C(CH₃)-- and Z=3-(CH₃)₃ Si-Ph; Y=--CH₂ O--N═C(NH₂)-- and Z=3-CF₃-Ph; Y=--CH₂ O--N═C(CH₃)-- and Z=3-CF₃ -Ph; or Y=--CH₂ O--N═C(CH₃)-- andZ=3,5-diBr-Ph.
 17. A compound of claim 1 having the formula ##STR121##wherein X=CH₃ O, Y=--CH₂ O--N═C(CH₃)-- and Z=3-CF₃ -Ph.
 18. A compoundof claim 1 which is selected from compounds having the formula##STR122## wherein Y=--CH₂ O--N═C(CH₃)-- and Z=3-(CH₃)₃ Si-Ph; Y=--CH₂O-- and Z=2,5-diCH₃ -Ph; Y=direct bond and Z=CH₂ Br; Y=--CH₂O--N═C(CH₃)-- and Z=3-CF₃ -Ph; Y=--CH═C(Cl)--C(═O)--O-- and Z=t-Bu; orY=--CH₂ O--N═C(CH₃)-- and Z=4-CF₃ -pyridin-2-yl.